1-(azolin-2-yl)amino-1,2-diphenylethane compounds for combating animal pests

ABSTRACT

The present invention relates to 1-(azolin-2-yl)amino-1,2-diphenylethane compounds of the formula I and to their salts which are useful for combating animal pests. The invention also relates to a method for controlling animal pests by using these compounds, to seed and to an agricultural and veterinary composition comprising said compounds. 
                         
wherein A is a radical of formulae A.1 or A.2
 
                         
wherein # denotes the bond to the remaining compound of formula I, X is selected from O, S and NR X ,
     R 1  is selected from the group consisting of —OR A , —NR B1 R B2 ,
       —C(═O)—R C , —C(═O)—OR D , —C(═O)—SR E , —C(═O)—NR B1 R B2 ′, —C(═S)—R C ′, —C(═S)—OR D ′, —C(═S)—SR E ′, —C(═S)—NR B1 R B2 , —C(═NR 1a )—R C ′, —C(═NR 1b )—OR D ′, —C(═NR 1c )—SR E ′, —C(═NR 1d )—NR B1 R B2 ,   —S(═O)—R F , —S(═O) 2 —R G , —S(═O) 2 —NR B1 R B2 ′, —P(═O)R H1 R H2 , —P(═S)R H1 R H2 , —B—C(═O)—R I , —B—O—C(═O)—R I , —B—S—C(═O)—R I , —B—N(R J )—C(═O)—R K , —B—C(═S)—R K , —B—O—C(═S)—R K , —B—S—C(═S)—R K , —B—N(R J )—C(═S)—R K ,   C 1 -C 8 -alkenyl, C 1 -C 8 -alkynyl, C 3 -C 8 -cycloalkyl, which is unsubstituted or may carry 1 to 4 substituents R 1e ,   naphthyl, which is unsubstituted or may carry 1 to 4 substituents R 1f ,   a saturated or partially unsaturated heterocycle, which is unsubstituted or may carry 1 to 4 substituents R 1g ,   hetaryl, which is unsubstituted or may carry 1 to 4 substituents R 1h , and   C 1 -C 6 -alkyl, which carries a radical selected from the group consisting of —NR 1i R 1j , C 1 -C 4 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, aryl, aryloxy, arylthio, heterocyclyl, heterocyclyloxy and heterocyclylthio,   
       R 2 , R 3 , R 4 , R 5 , R 6  and R 7  are each independently hydrogen, halogen, OH, SH, NH 2 , SO 3 H, COOH, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylamino etc.

This application is a National Stage application of International Application No. PCT/EP2008/058517 filed Jul. 2, 2008, which claims the benefit of U.S. Provisional Application No. 60/958,134, filed Jul. 3, 2007, the entire contents of which is hereby incorporated herein by reference.

The present invention relates to 1-(azolin-2-yl)amino-1,2-diphenylethane compounds which are useful for combating animal pests. The invention also relates to a method for controlling animal pests by using these compounds, to seed and to an agricultural and veterinary composition comprising said compounds.

Animal pests and in particular arthropods and nematodes destroy growing and harvested crops and attack wooden dwelling and commercial structures, causing large economic loss to the food supply and to property. While a large number of pesticidal agents are known, due to the ability of target pests to develop resistance to said agents, there is an ongoing need for new agents for combating insects, arachnids and nematodes. It is therefore an object of the present invention to provide compounds having a good pesticidal activity and showing a broad activity spectrum against a large number of different animal pests, especially against difficult to control insects, arachnids and nematodes.

Jennings et al. Pesticide Biochemistry and Physiology 30, 1988, p. 190-197 describe several 2-phenylamino oxazolines and 2-benzylamino oxazolines which have insecticidal activity. Biosci. Biotech. Biochem. 1992, 56 (7), 1062-1065 discloses phenyl-, benzyl- and phenethyl thiazolines having insecticidal activity. However, these compounds are limited in their activity or with regard to breadth of their activity spectrum.

The WO 2005/063724 describes 1-(azolin-2-yl)amino-1,2-diphenylethane compounds of the general formulae C.1 and C.2,

wherein X is sulfur or oxygen, which are useful for combating insects, arachnids and nematodes.

It is an object of the present invention to provide compounds that have a good pesticidal activity, in particular insecticidal activity, and show a broad activity spectrum against a large number of different animal pests, especially against difficult to control insects.

It has been found that these objectives can be achieved by compounds of the formula I below.

Therefore, in a first aspect, the invention relates to compounds of formula I

wherein

-   A is a radical of formulae A.1 or A.2

-    wherein # denotes the bond to the remaining compound of formula I -   X is selected from O, S and NR^(X), wherein     -   R^(X) is selected from hydrogen, cyano, nitro, C₁-C₃-alkyl,         C₁-C₃-alkoxy, C₁-C₃-haloalkyl, C₁-C₃-haloalkoxy, formyl,         C₁-C₆-alkylcarbonyl and C₁-C₆-alkoxycarbonyl; -   R¹ is selected from the group consisting of —OR^(A), —NR^(B1)R^(B2),     -   —C(═O)—R^(C), —C(═O)—OR^(D), —C(═O)—SR^(E),         —C(═O)—NR^(B1)R^(B2)′, —C(═S)—R^(C)′, —C(═S)—OR^(D)′,         —C(═S)—SR^(E)′, —C(═S)—NR^(B1)R^(B2), —C(═NR^(1a))—R^(C)′,         —C(═NR^(1b))—OR^(D)′, —C(═NR^(1c))—SR^(E)′,         —C(═NR^(1d))—NR^(B1)R^(B2),     -   —S(═O)—R^(F), —S(═O)₂—R^(G), —S(═O)₂—NR^(B1)R^(B2)′,         —P(═O)R^(H1)R^(H2), —P(═S)R^(H1)R^(H2), —B—C(═O)—R^(I),         —B—O—C(═O)—R^(I), —B—S—C(═O)—R^(I), —B—N(R^(J))—C(═O)—R^(K),         —B—C(═S)—R^(K), —B—O—C(═S)—R^(K), —B—S—C(═S)—R^(K),         —B—N(R^(J))—C(═S)—R^(K),     -   C₁-C₈-alkenyl, C₁-C₈-alkynyl, C₃-C₈-cycloalkyl, which is         unsubstituted or may carry 1 to 4 substituents R^(1e),     -   naphthyl, which is unsubstituted or may carry 1 to 4         substituents R^(1f),     -   a saturated or partially unsaturated heterocycle, which is         unsubstituted or may carry 1 to 4 substituents R^(1g),     -   hetaryl, which is unsubstituted or may carry 1 to 4 substituents         R^(1h), and     -   C₁-C₆-alkyl, which carries a radical selected from the group         consisting of —NR^(1i)R^(1j), C₁-C₄-alkoxycarbonyl,         C₃-C₈-cycloalkyl, aryl, aryloxy, arylthio, heterocyclyl,         heterocyclyloxy and heterocyclylthio, wherein the alkyl,         cycloalkyl, aryl or heterocyclyl moieties of the last 8         mentioned radicals may carry 1, 2, 3 or four radicals selected         from CN, NO₂, halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy,         C₁-C₃-haloalkyl, C₁-C₃-haloalkoxy and C₃-C₈-cycloalkyl, wherein     -   B is linear or branched C₁-C₄-alkylene, which is unsubstituted         or may carry 1, 2, 3 or 4 radicals selected from halogen and         C₁-C₃-alkoxy,     -   R^(A) is selected from the group consisting of hydrogen,         C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the last         three mentioned radicals may carry 1, 2, 3 or 4 substituents         selected independently from halogen, C₁-C₃-alkoxy,         C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio and         C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl which is unsubstituted or may         carry 1, 2, 3 or 4 substituents R^(1e), naphthyl which is         unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1f), and         hetaryl which is unsubstituted or may carry 1, 2, 3 or 4         substituents R^(1h),     -   R^(B1), R^(B2) are selected independently from the group         consisting of hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,         C₂-C₆-alkynyl, wherein the last three mentioned radicals may         carry 1, 2, 3 or 4 substituents selected independently from         halogen, C₁-C₃-alkoxy, C₁-C₃-haloalkoxy, C₁-C₃-alkylthio,         C₁-C₃-haloalkylthio and C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl which         is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1e),         phenyl which is unsubstituted or may carry 1, 2, 3 or 4         substituents R^(1f), naphthyl which is unsubstituted or may         carry 1, 2, 3 or 4 substituents R^(1f), and hetaryl which is         unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1h),     -   R^(B2)′ is selected from the group consisting of         C₃-C₈-cycloalkyl which is unsubstituted or may carry 1, 2, 3 or         4 substituents R^(1e), phenyl which is unsubstituted or may         carry 1, 2, 3 or 4 substituents R^(1f), naphthyl which is         unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1f), and         hetaryl which is unsubstituted or may carry 1, 2, 3 or 4         substituents R^(1h),     -   R^(C) is selected from, C₁-C₆-alkyl which carries 1, 2, 3 or 4         radicals selected from C(═O)OH, aryloxy, hetaryloxy, arylthio,         hetarylthio or C₁-C₄-alkoxy-carbonyl, wherein the five last         mentioned radicals are unsubstituted or may carry 1, 2, 3 or 4         groups selected independently from CN, NO₂, halogen,         C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl, C₁-C₃-haloalkoxy and         C₃-C₈-cycloalkyl,     -   R^(C)′ is selected from the group consisting of hydrogen,         C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the last         three mentioned radicals may carry 1, 2, 3 or 4 substituents         selected independently from halogen, C₁-C₃-alkoxy,         C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio and         C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl which is unsubstituted or may         carry 1, 2, 3 or 4 substituents R^(1e), phenyl which is         unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1f),         naphthyl which is unsubstituted or may carry 1, 2, 3 or 4         substituents R^(1f), and hetaryl which is unsubstituted or may         carry 1, 2, 3 or 4 substituents R^(1h),     -   R^(D), R^(E) are selected from the group consisting of         C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the last two mentioned         radicals may carry 1, 2, 3 or 4 substituents selected         independently from halogen, C₁-C₃-alkoxy, C₁-C₃-haloalkoxy,         C₁-C₃-alkylthio, C₁-C₃-haloalkylthio and C₃-C₈-cycloalkyl,         C₃-C₈-cycloalkyl which is unsubstituted or may carry 1, 2, 3 or         4 substituents R^(1e), phenyl which is unsubstituted or may         carry 1, 2, 3 or 4 substituents R^(1f), naphthyl which is         unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1f), and         hetaryl which is unsubstituted or may carry 1, 2, 3 or 4         substituents R^(1h),     -   R^(D)′, R^(E)′, R^(E)′, R^(G), R^(H1), R^(H2) have one of the         meanings given for R^(D), R^(E) or are selected from hydrogen or         C₁-C₆-alkyl, which is unsubstitued or carries 1, 2, 3 or 4         substituents selected independently from halogen, C₁-C₃-alkoxy,         C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio and         C₃-C₈-cycloalkyl,     -   R^(I), R^(K) are selected from the group consisting of         C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the last         three mentioned radicals may carry 1, 2, 3 or 4 substituents         selected independently from halogen, C₁-C₃-alkoxy,         C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio and         C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl which is unsubstituted or may         carry 1, 2, 3 or 4 substituents R^(1e), phenyl which is         unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1f),         naphthyl which is unsubstituted or may carry 1, 2, 3 or 4         substituents R^(1f), and hetaryl which is unsubstituted or may         carry 1, 2, 3 or 4 substituents R^(1h),     -   R^(J) is selected from the group consisting of hydrogen,         C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the last         three mentioned radicals may carry 1, 2, 3 or 4 substituents         selected independently from halogen, C₁-C₃-alkoxy,         C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio and         C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl which is unsubstituted or may         carry 1, 2, 3 or 4 substituents R^(1e), phenyl which is         unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1f),         naphthyl which is unsubstituted or may carry 1, 2, 3 or 4         substituents R^(1f), and hetaryl which is unsubstituted or may         carry 1, 2, 3 or 4 substituents R^(1h),     -   R^(1a), R^(1b), R^(1c) and R^(1d) is selected from hydrogen         C₁-C₃-alkyl, C₁-C₃-alkoxy, C₃-C₈-cycloalkyl, C₂-C₃-alkenyl and         C₂-C₃-alkenyloxy,     -   R^(1e), R^(1g) are independently of one another selected from         C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy,     -   R^(1f), R^(1h) are independently of one another selected from         CN, NO₂, halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl,         C₁-C₃-haloalkoxy and C₃-C₈-cycloalkyl,     -   R^(1i) is selected from hydrogen, C₁-C₃-alkyl, C₁-C₃-alkoxy,         C₃-C₈-cycloalkyl, C₂-C₃-alkenyl and C₂-C₃-alkenyloxy, and     -   R^(1j) is selected from C₁-C₃-alkyl, C₁-C₃-alkoxy,         C₃-C₈-cycloalkyl, C₂-C₃-alkenyl and C₂-C₃-alkenyloxy, and -   R², R³, R⁴, R⁵, R⁶ and R⁷ are each independently hydrogen, halogen,     OH, SH, NH₂, SO₃H, COOH, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-alkoxy,     C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₈-alkylthio,     C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkenylamino,     C₂-C₆-alkenylthio, C₂-C₆-alkynyl, C₂-C₆-alkynyloxy,     C₂-C₆-alkynylamino, C₂-C₆-alkynylthio, C₁-C₆-alkylsulfonyl,     C₁-C₆-alkylsulfoxyl, C₂-C₆-alkenylsulfonyl, C₂-C₆-alkynylsulfonyl,     formyl, C₁-C₆-alkylcarbonyl, C₂-C₆-alkenylcarbonyl,     C₂-C₆-alkynylcarbonyl, C₁-C₆-alkoxycarbonyl,     C₂-C₆-alkenyloxycarbonyl, C₂-C₆-alkynyloxycarbonyl, carbonyloxy,     C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkenylcarbonyloxy,     C₁-C₆-alkynylcarbonyloxy, wherein the carbon atoms in the aliphatic     radicals of the aforementioned groups may carry any combination of     1, 2 or 3 radicals selected from the group consisting of halogen,     cyano, nitro, hydroxy, mercapto, amino, carboxyl, C₁-C₆-alkyl,     C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy     and C₁-C₆-alkylthio,     -   C(O)NR^(L)R^(M), (SC₂)NR^(L)R^(M), wherein R^(L) and R^(M) are         each independently hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, or         C₂-C₆-alkynyl, wherein the carbon atoms in these groups may         carry any combination of 1, 2 or 3 radicals selected from the         group consisting of halogen, cyano, nitro, hydroxy, mercapto,         amino, carboxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy,         C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy and C₁-C₆-alkylthio,     -   a radical Y—Ar or a radical Y-Cy, wherein     -   Y is a single bond, oxygen, sulfur, C₁-C₆-alkanediyl or         C₁-C₆-alkanediyloxy,     -   Ar is phenyl, naphthyl or a mono- or bicyclic 5- to 10-membered         heteroaromatic ring, which contains 1,2, 3 or 4 heteroatoms         se-lected from oxygen, sulfur and nitrogen as ring members,         wherein Ar is unsubstituted or may carry any combination of 1,         2, 3, 4 or 5 radicals selected from the group consisting of         halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl,         C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy,         C₁-C₆-haloalkoxy and C₁-C₆-alkylthio; and     -   Cy is C₃-C₁₂-cycloalkyl, which is unsubstituted or substituted         with any combination of 1, 2, 3, 4 or 5 radicals selected from         the group consisting of halogen, cyano, nitro, hydroxy,         mercapto, amino, carboxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy,         C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy and         C₁-C₆-alkylthio;     -   and wherein two radicals R², R³, R⁴, R⁵ or R⁶ that are bound to         adjacent carbon atoms of the phenyl rings may form together with         said carbon atoms a fused benzene ring, a fused saturated or         partially un-saturated 5-, 6-, or 7-membered carbocycle or a         fused 5-, 6-, or 7-membered heterocycle, which contains 1, 2, 3         or 4 heteroatoms selected from O, S and N as ring members, and         wherein the fused ring is unsubstituted or may carry any         combination of 1, 2, 3, or 4 radicals selected from the group         consisting of halogen, cyano, nitro, hydroxy, mercapto, amino,         carboxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy,         C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy and C₁-C₆-alkylthio;

or the enantiomers, diastereomers or salts thereof.

Another object of the present invention is the use of the compounds of formula I as defined above or of a salt thereof for combating animal pests.

Another object of the present invention is an agricultural composition containing at least one compound of the formula I as defined above and/or an agriculturally acceptable salt thereof and at least one liquid or solid carrier.

Another object of the present invention is a veterinary composition containing at least one compound of the formula I as defined above and/or a veterinarily acceptable salt thereof and at least one veterinarily acceptable liquid or solid carrier.

The present invention also provides a method for controlling animal pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or a plant, plant propagation material, soil, area, material or environment in which the pests are growing or may grow, or the materials, plants, plant propagation material, soils, surfaces or spaces to be protected from pest attack or infestation with a pesticidally effective amount of a com-pound of the formula I or a salt thereof or a composition as defined above.

The invention further related to a method for treating or protecting an animal from infestation or infection by parasites which comprises bringing the animal in contact with a parasiticidally effective amount of a compound of the formula I or a veterinally acceptable salt thereof as defined above. Bringing the animal in contact with the compound I, its salt or the veterinary composition of the invention means applying or administering it to the animal.

A further object of the present invention is plant propagation material, in particular seed, comprising at least one compound of formula I and/or an agriculturally acceptable salt thereof.

In the compounds of formula I, the carbon atom which carries the radical A creates a center of chirality. Thus, the compound of formula I may be present in the form of different enantiomers or if another center of chirality is present in any of the radicals R² to R⁷, it may exist in the form of diastereomers. In case that A is a radical of the formula A.2, the compound I may also exist as a cis- or trans-isomer with respect to the N═C axis. The present invention relates to every possible stereoisomer of the compounds of formula I, i.e. to single enantiomers or diastereomers, as well as to mixtures thereof.

The compounds of the present invention may be amorphous or may exist in one ore more different crystalline states (polymorphs) which may have a different macroscopic properties such as stability or show different biological properties such as activities. The present invention includes both amorphous and crystalline compounds of the formula I, mixtures of different crystalline states of the respective compound I, as well as amorphous or crystalline salts thereof.

Salts of the compounds of the formula I are preferably agriculturally and veterinarily acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula I has a basic functionality or by reacting an acidic compound of formula I with a suitable base.

Suitable agriculturally useful salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention. Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NH⁴⁺) and substituted ammonium in which one to four of the hydrogen atoms are replaced by C₁-C₄-alkyl, C₁-C₄-hydroxyalkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl. Examples of substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C₁-C₄-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound of formulae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

By the term “veterinarily acceptable salts” is meant salts of those cations or anions which are known and accepted in the art for the formation of salts for veterinary use. Suitable acid addition salts, e.g. formed by compounds of formula I containing a basic nitrogen atom, e.g. an amino group, include salts with inorganic acids, for example hydrochlorids, sulphates, phosphates, and nitrates and salts of organic acids for example acetic acid, maleic acid, dimaleic acid, fumaric acid, difumaric acid, methane sulfenic acid, methane sulfonic acid, and succinic acid.

The term “plant propagation material” includes any parts of a plant which are propagable. In general, a plant propagation material is the product of the ripened ovule of gymnosperm and angiosperm plants which occurs after fertilization and some growth within the mother plant and includes seed, fruits, spurious fruits, infructescences and also rhizomes (rootstocks), corms, tubers, bulbs and scions. In particular, the term “plant propagation material” has to be understood as seed.

The organic moieties mentioned in the above definitions of the variables are—like the term halogen—collective terms for individual listings of the individual group members. The prefix C_(n)-C_(m) indicates in each case the possible number of carbon atoms in the group.

The term halogen denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.

Examples of other meanings are:

The term “C₁-C₆-alkyl” as used herein and in the alkyl moieties of C₁-C₆-alkoxy, C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio and C₁-C₆-alkylcarbonyloxy refers to a saturated straight-chain or branched hydrocarbon group having 1 to 6 carbon atoms, especially 1 to 3 carbon groups (═C₁-C₃-alkyl). Examples for C₁-C₃-alkyl are methyl, ethyl, propyl and 1-methylethyl(isopropyl). Examples for C₁-C₆-alkyl further encompass, butyl, 1-methylpropyl(sec-butyl, 2-butyl), 2-methylpropyl(iso-butyl), 1,1-dimethylethyl(tert-butyl), pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methyl pentyl, 2-methylpentyl, 3 methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methyl propyl.

The term “C₁-C₆-haloalkyl” as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 6 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as men-tioned above, for example C₁-C₃-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1 fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2 chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and the like.

The term “C₁-C₆-alkoxy” as used herein and in the term C₁-C₆-alkoxycarbonyl refers to a straight-chain or branched saturated alkyl group having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms (C₁-C₃-alkoxy) (as mentioned above) which is attached via an oxygen atom. Examples for C₁-C₃-alkoxy include methoxy, ethoxy, OCH₂—C₂H₅ (propoxy) and OCH(CH₃)₂ (isopropoxy). Examples for C₁-C₆-alkoxy further encompass n-butoxy, OCH(CH₃)C₂H₅ (sec-butoxy), OCH₂CH(CH₃)₂ (isobutoxy), OC(CH₃)₃ (tert-butoxy), n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethyl-propoxy, 1,2-dimethylpropoxy, 2,2-dimethyl-propoxy, 1-ethylpropoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethyl-butoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethyl-butoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, 1-ethyl-2-methylpropoxy and the like.

The term “C₁-C₆-haloalkoxy” as used herein refers to a C₁-C₆-alkoxy group as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine. Preferred are C₁-C₃-haloalkoxy groups, i.e. C₁-C₃-alkoxy groups as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy and 1-(bromomethyl)-2-bromo-ethoxy. Examples for C₁-C₆-haloalkoxy further encompass 4-fluorobutoxy, 4-chloro-butoxy, 4-bromobutoxy, nonafluorobutoxy, 5-fluoro-1-pentoxy, 5-chloro-1-pentoxy, 5-bromo-1-pentoxy, 5-iodo-1-pentoxy, 5,5,5-trichloro-1-pentoxy, undecafluoropentoxy, 6-fluoro-1-hexoxy, 6-chloro-1-hexoxy, 6-bromo-1-hexoxy, 6-iodo-1-hexoxy, 6,6,6-trichloro-1-hexoxy and dodecafluorohexoxy. Particularly preferred are chloromethoxy, fluorometh-oxy, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy and 2,2,2-trifluoroethoxy.

The term “C₁-C₆-alkylcarbonyl” as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms (═C₁-C₄-alkylcarbonyl) (as mentioned above) bonded via the carbon atom of the carbonyl group at any bond in the alkyl group. Examples for C₁-C₄-alkylcarbonyl include C(O)CH₃, C(O)C₂H₅, n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-methyl propylcarbonyl, 2-methylpropylcarbonyl and 1,1-dimethylethylcarbonyl. Examples for C₁-C₆-alkylcarbonyl further encompass n-pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, n-hexylcarbonyl, 1-methyl pentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl, 2,3-dimethyl butylcarbonyl, 3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl and the like.

The term “C₁-C₆-alkoxycarbonyl” as used herein refers to a straight-chain or branched alkoxy group (as mentioned above) having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms (═C₁-C₄-alkoxycarbonyl) attached via the carbon atom of the carbonyl group (R—O—C(O)—; R=alkyl). Examples for C₁-C₄-alkoxycarbonyl include C(O)OCH₃, C(O)OC₂H₅, C(O)O—CH₂—C₂H₅, C(O)OCH(CH₃)₂, n-butoxycarbonyl, C(O)OCH(CH₃)—C₂H₅, C(O)OCH₂CH(CH₃)₂ and C(O)OC(CH₃)₃. Examples for C₁-C₆-alkoxycarbonyl further encompass n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3 methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n hexoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3 dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethyl butoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1,2 trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl, 1-ethyl-1-methylpropoxycarbonyl or 1-ethyl-2-methylpropoxycarbonyl.

The term “C₁-C₆-alkylcarbonyloxy” as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms (═C₁-C₄-alkylcarbonyloxy) (as mentioned above) bonded via the carbon atom of the carbonyloxy group at any bond in the alkyl group. Examples for C₁-C₄-alkylarbonyloxy include O—CO—CH₃, O—CO—C₂H₅, n-propylcarbonyloxy, 1-methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-ethylpropylcarbonyloxy and 1,1-dimethylethylcarbonyloxy. Examples for C₁-C₆-alkylcarbonyloxy further encompass n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2-methyl butylcarbonyloxy, 3-methylbutylcarbonyloxy, 1,1-dimethylpropylcarbonyloxy or 1,2-dimethylpropylcarbonyloxy.

The term “C₁-C₆-alkylthio “(C₁-C₆-alkylsulfanyl: C₁-C₆-alkyl-S—)” as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms (═C₁-C₃-alkylthio) (as mentioned above) which is attached via a sulfur atom. Examples for C₁-C₃-alkylthio include methylthio, ethylthio, propylthio and 1-methylethylthio. Examples for C₁-C₆-alkylthio further encompass butylthio, 1-methylpropylthio, 2-methylpropylthio and 1,1-dimethylethylthio. n-pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, n-hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutythio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutlthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio.

The term “C₁-C₆-haloalkylthio” as used herein refers to a C₁-C₆-alkylthio group as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine. Preferred are C₁-C₃-haloalkylthio groups, i.e. C₁-C₃-alkylthio groups as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoro-methylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, pentafluoroethyl-thio, 2-fluoropropylthio, 3-fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2,3-dichloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio, heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio, 1-(chloromethyl)-2-chloroethylthio or 1-(bromomethyl)-2-bromoethylthio. Examples for C₁-C₆-haloalkylthio further encompass 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio, nonafluorobutylthio, 5-fluoro-1-pentylthio, 5-chloro-1-pentylthio, 5-bromo-1-pentylthio, 5-iodo-1-pentylthio, 5,5,5-trichloro-1-pentylthio, undecafluoropentylthio, 6-fluoro-1-hexylthio, 6-chloro-1-hexylthio, 6-bromo-1-hexylthio, 6-iodo-1-hexylthio, 6,6,6-trichloro-1-hexylthio and dodecafluorohexylthio. Particularly preferred are chloromethyl-thio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio and 2,2,2-trifluoroethylthio.

The term “C₁-C₆-alkylsulfoxyl” (C₁-C₆-alkylsulfinyl: C₁-C₆-alkyl-S(═O)—), as used herein refers to a straight-chain or branched saturated alkyl group (as mentioned above) having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms (═C₁-C₄-alkylsulfoxyl) bonded through the sulfur atom of the sulfoxyl group at any position in the alkyl group. Exam-ples for C₁-C₄-alkylsulfoxyl include S(O)CH₃, S(O)C₂H₅, n-propylsulfinyl, 1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl and 1,1-dimethylethylsulfinyl. Examples for C₁-C₆-alkylsulfinyl further encompass n-pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3 methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2 dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, n-hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2 dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1 ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2 trimethylpropylsulfinyl, 1-ethyl-1-methyl propylsulfinyl and 1-ethyl-2-methyl propylsulfinyl.

The term “C₁-C₆-alkylsulfonyl” (C₁-C₆-alkyl-S(═O)₂—) as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms (═C₁-C₄-alkylsulfonyl) (as mentioned above) which is bonded via the sulfur atom of the sulfonyl group at any position in the alkyl group. Examples for C₁-C₄-alkylsulfonyl include SC₂—CH₃, SC₂—C₂H₅, n-propylsulfonyl, SC₂—CH(CH₃)₂, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl and SO₂—C(CH₃)₃. Examples for C₁-C₆-alkylsulfonyl further encompass n pentylsulfonyl, 1-methylbutyl-sulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, n-hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2 dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3 dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2 ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl.

The term “C₁-C₆-alkylamino” refers to a secondary amino group carrying one alkyl group as defined above, e.g. methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino, 1,1-dimethylethylamino, pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino, 1-ethylpropylamino, hexylamino, 1,1-dimethylpropylamino, 1,2-dimethylpropylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino, 1-ethyl-1-methylpropylamino or 1-ethyl-2-methylpropylamino.

The term “di(C₁-C₆-alkyl)amino)” refers to a tertiary amino group carrying two alkyl radicals as defined above, e.g. dimethylamino, diethylamino, di-n-propylamino, diisopropylamino, N-ethyl-N-methylamino, N-(n-propyl)-N-methylamino, N-(isopropyl)-N-methylamino, N-(n-butyl)-N-methylamino, N-(n-pentyl)-N-methylamino, N-(2-butyl)-N-methylamino, N-(isobutyl)-N-methylamino, N-(n-pentyl)-N-methylamino, N-(n-propyl)-N-ethylamino, N-(isopropyl)-N-ethylamino, N-(n-butyl)-N-ethylamino, N-(n-pentyl)-N-ethylamino, N-(2-butyl)-N-ethylamino, N-(isobutyl)-N-ethylamino and the like.

The term “C₂-C₆-alkenyl” as used herein and in the alkenyl moieties of C₂-C₆-alkenyloxy, C₂-C₆-alkenylamino, C₂-C₆-alkenylthio, C₂-C₆-alkenylsulfonyl, C₂-C₆-alkenylcarbonyl, C₂-C₆-alkenyloxycarbonyl and C₂-C₆-alkenylcarbonyloxy refers to a straight-chain or branched unsaturated hydrocarbon group having 2 to 6 carbon atoms and a double bond in any position, such as ethenyl, 1-propenyl, 2 propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2 methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl; 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1 methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2 methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1 propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3 methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3 methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3 methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3 butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3 dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3 butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3 dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1 ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2 trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl.

The term, “C₂-C₆-alkenyloxy” as used herein refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms (as mentioned above) which is attached via an oxygen atom, such as vinyloxy, allyloxy (propen-3-yloxy), methallyloxy, buten-4-yloxy and the like.

The term “C₂-C₆-alkenylthio” as used herein refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms (as mentioned above) which is attached via a sulfur atom, for example vinylsulfanyl, allylsulfanyl (propen-3-ylthio), methallylsufanyl, buten-4-ylsulfanyl and the like.

The term “C₂-C₆-alkenylcarbonyl” as used herein refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms (as mentioned above) which is bonded via the carbon atom of the carbonyl group at any bond in the alkenyl group, for example vinylcarbonyl, allylcarbonyl (propen-3-ylcarbonyl), methallylcarbonyl, buten-4-yl-carbonyl and the like.

The term “C₂-C₆-alkenyloxycarbonyl” as used herein refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms (as mentioned above) which is bonded via the carbon atom of the oxycarbonyl group (RO—C(O)—; R═C₂-C₆-alkenyl), for example vinyloxycarbonyl, allyloxycarbonyl (propen-3-yloxycarbonyl), methallyloxycarbonyl, buten-4-yloxycarbonyl and the like.

The term “C₂-C₆-alkenylcarbonyloxy” as used herein refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms (as mentioned above) which is bonded via the oxygen atom of the carbonyloxy group (R—C(O)—O—; R═C₂-C₆-alkenyl), for example vinylcarbonyloxy, allylcarbonyloxy (propen-3-ylcarbonyloxy), methallylcarbonyloxy, buten-4-ylcarbonyloxy and the like.

The term “C₂-C₆-alkenylamino” as used herein refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms (as mentioned above) which is attached via a sulfur atom, for example vinylamino, allylamino (propen-3-ylamino), methallylamino, buten-4-ylamino and the like.

The term “C₂-C₆-alkenylsulfonyl” as used herein refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms (as mentioned above) which is attached via a sulfonyl group (SO₂), for example vinylsulfonyl, allylsulfonyl(propen-3-ylsulfonyl), methallylsufonyl, buten-4-ylsulfonyl and the like.

The term “C₂-C₆-alkynyl” as used herein and in the alkynyl moieties of C₂-C₆-alkynyloxy, C₂-C₆-alkynylamino, C₂-C₆-alkynylthio, C₂-C₆-alkynylsulfonyl, C₂-C₆-alkynylcarbonyl, C₂-C₆-alkynyloxycarbonyl and C₂-C₆-alkynylcarbonyloxy refers to a straight-chain or branched unsaturated hydrocarbon group having 2 to 6 carbon atoms and containing at least one triple bond, such as ethynyl, prop-1-yn-1-yl, prop-2-yn-1-yl, n-but-1-yn-1-yl, n-but-1-yn-3-yl, n-but-1-yn-4-yl, n-but-2-yn-1-yl, n-pent-1-yn-1-yl, n-pent-1-yn-3-yl, n-pent-1-yn-4-yl, n-pent-1-yn-5-yl, n-pent-2-yn-1-yl, n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl, n-hex-1-yn-1-yl, n-hex-1-yn-3-yl, n-hex-1-yn-4-yl, n-hex-1-yn-5-yl, n-hex-1-yn-6-yl, n-hex-2-yn-1-yl, n-hex-2 yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-yn-1-yl, n-hex-3-yn-2-yl, 3-methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-1-yn-1-yl, 4-methyl pent-2-yn-4-yl or 4-methyl pent-2-yn-5-yl and the like.

The term, “C₂-C₆-alkynyloxy” as used herein refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms (as mentioned above) which is attached via an oxygen atom, such as propargyloxy(propyn-3-yloxy), butyn-3-yloxy, butyn-4-yloxy and the like.

The term “C₂-C₆-alkynylthio” as used herein refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms (as mentioned above) which is attached via a sulfur atom, such as propargylsulfanyl(propyn-3-ylthio), butyn-3-ylsufanyl, butyn-4-ylsulfanyl and the like.

The term “C₂-C₆-alkynylcarbonyl” as used herein refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms (as mentioned above) which is bonded via the carbon atom of the carbonyl group at any bond in the alkynyl group, for example propargylcarbonyl(propyn-3-ylcarbonyl), butyn-3-ylcarbonyl, butyn-4-ylcarbonyl and the like.

The term “C₂-C₆-alkynyloxycarbonyl” as used herein refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms (as mentioned above) which is bonded via the carbon atom of the oxycarbonyl group (RO—C(O)—; R═C₂-C₆-alkynyl), for example propargyloxycarbonyl(propyn-3-yloxycarbonyl), butyn-3-yloxycarbonyl, butyn-4-yloxycarbonyl and the like.

The term “C₂-C₆-alkynylcarbonyloxy” as used herein refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms (as mentioned above) which is bonded via the oxygen atom of the carbonyloxy group (R—C(O)—O—; R═C₂-C₆-alkynyl), for example propargylcarbonyloxy (propyn-3-ylcarbonyloxy), butyn-3-ylcarbonyloxy, butyn-4-ylcarbonyloxy and the like.

The term “C₂-C₆-alkynylamino” as used herein refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms (as mentioned above) which is attached via a sulfur atom, such as propargylamino(propyn-3-ylamino), butyn-3-amino, butyn-4-ylamino and the like.

The term “C₂-C₆-alkynylsulfonyl” as used herein refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms (as mentioned above) which is attached via a sulfonyl (SO₂) group, such as propargylsulfonyl(propin-3-yltsulfonyl), butyn-3-ylsufonyl butyn-4-ylsulfonyl and the like.

The term “C₃-C₁₂-cycloalkyl” as used herein refers to a mono- or bi- or polycyclic hydrocarbon radical having 3 to 12 (═C₃-C₁₂-cycloalkyl), frequently 3 to 8 carbon atoms (═C₃-C₈-cycloalkyl), in particular 3 to 6 carbon atoms (═C₃-C₆-cycloalkyl). Examples of monocyclic radicals comprise cyclo-propyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl. Examples of bicyclic radicals comprise bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl.

The term “aryl” as used herein refers to a C₆-C₁₄ carboaromatic group, such as phenyl, naphthyl, anthracenyl and phenanthrenyl. Preferably, aryl is phenyl.

The term “aryloxy” refers to aryl as defined above which is bound via an oxygen atom to the remainder of the molecule. Examples are phenoxy and naphthoxy.

The term “arylthio” refers to aryl as defined above which is bound via a sulfur atom to the remainder of the molecule. Examples are phenoxy and naphthoxy.

Phenyl fused to phenyl is naphthyl.

Phenyl fused to a 5- or 6-membered non-aromatic (i.e. saturated or partially unsaturated) heterocyclic ring is for example 2,3-dihydrobenzofuranyl, benzoxolanyl, 2,3-dihydrobenzothienyl, indolinyl, chromanyl, chromenyl, benzodioxanyl and the like. Ex-amples for phenyl fused to a 5- or 6-membered aromatic heterocyclic ring (=fused to a 5- or 6-membered heteroaromatic ring) are given below.

The term “hetaryl” (“momo or bicyclic 5- to 10-membered heteroaromatic ring”) as used herein refers to a monocyclic heteroaromatic radical which has 5 or 6 ring members, which may be fused to a carbocyclic or heterocyclic 5, 6 or 7 membered ring thus having a total number of ring members from 8 to 10, wherein in each case 1, 2, 3 or 4, preferably 1, 2 or 3, of these ring members are heteroatoms selected, independently from each other, from the group consisting of oxygen, nitrogen and sulfur. The heteraryl radical may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member. The carbocyclic or heterocyclic fused ring is selected from C₅-C₇-cycloalkyl, 5 to 7 membered heterocyclyl and phenyl.

Examples for monocyclic 5- to 6-membered heteroaromatic rings include triazinyl, pyrazinyl, pyrimidyl, pyridazinyl, pyridyl, thienyl, furyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, thiazolyl, oxazolyl, thiadiazolyl, oxadiazolyl, isothiazolyl and isoxazolyl.

Examples for 5- to 6-membered heteroaromatic rings being fused to a phenyl ring (or for a phenyl ring fused to a 5- to 6-membered heteroaromatic ring) are quinolinyl, isoquinolinyl, indolyl, indolizinyl, isoindolyl, indazolyl, benzofuryl, benzthienyl, benzo[b]thiazolyl, benzoxazolyl, benzthiazolyl, benzoxazolyl, and benzimidazolyl. Examples for 5- to 6-membered heteroaromatic rings being fused to a cycloalkenyl ring are dihydroindolyl, dihydroindolizinyl, dihydroisoindolyl, dihydrochinolinyl, dihydroisochinolinyl, chromenyl, chromanyl and the like.

The term “hetaryloxy” refers to hetaryl as defined above which is bound via an oxygen atom to the remainder of the molecule.

The term “hetarylthio” refers to hetaryl as defined above which is bound via a sulfur atom to the remainder of the molecule.

The term “heterocyclyl” (“saturated or partially unsaturated heterocycle”) comprises nonaromatic saturated or partially unsaturated heterocyclic rings having 5 or 6 ring members and 1, 2, 3 or 4, preferably 1, 2 or 3 heteroatoms as ring members. The heterocyclic radical may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member. Examples for non-aromatic rings include pyrrolidinyl, pyrazolinyl, imidazolinyl, pyrrolinyl, pyrazolinyl, imidazolinyl, tetrahydrofuranyl, dihydrofuranyl, 1,3-dioxolanyl, dioxolenyl, thiolanyl, dihydrothienyl, oxazolidinyl, isoxazolidinyl, oxazolinyl, isoxazolinyl, thiazolinyl, isothiazolinyl, thiazolidinyl, isothiazolidinyl, oxathiolanyl, piperidinyl, piperazinyl, pyranyl, dihydropyranyl, tetrahydropyranyl, 1,3- and 1,4-dioxanyl, thiopyranyl, dihydrothiopyranyl, tetrahydrothiopyranyl, morpholinyl, thiazinyl and the like. Examples for heterocyclic ring also comprising 1 or 2 carbonyl groups as ring members comprise pyrrolidin-2-onyl, pyrrolidin-2,5-dionyl, imidazolidin-2-onyl, oxazolidin-2-onyl, thiazolidin-2-onyl and the like.

The term “heterocyclyloxy” refers to heterocyclyl as defined above which is bound via an oxygen atom to the remainder of the molecule.

The term “heterocyclylthio” refers to heterocyclyl as defined above which is bound via a sulfur atom to the remainder of the molecule.

The term “linear or branched C₁-C₆-alkanediyl” as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 6 carbon atoms (as mentioned above), where one of the hydrogen atoms in these groups is replaced by a further bonding position. Examples for linear C₁-C₆-alkanediyl comprise methyldiyl, ethane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl. Examples for branched C₁-C₆-alkanediyl comprise ethyl-1,1-diyl, propyl-1,1-diyl, butyl-1,1-diyl, 1-methylethane-1,2-diyl, 1,2-dimethylethane-1,2-diyl, 1-ethylethane-1,2-diyl, 1-methylpropane-1,3-diyl, 2-methylpropan-1,3-diyl and the like.

The group of compounds of formula I includes compounds, wherein A is a radical of formula A.1, referred to as compounds of formula I.1, and compounds, wherein A is a radical of formula A.2, referred to as compounds of formula I.2.

A preferred embodiment of the invention relates to compounds of the formula I.1, as shown herein.

The remarks made below concerning preferred embodiments of the variables of the compounds of formula I as well as of formulae I.1 and I.2, of the features of the use and method according to the invention and of the composition of the invention are valid on their own as well as preferably in combination with each other.

The group X is preferably a sulfur atom.

Preferably, R¹ is selected from the group consisting of —C(═O)—R^(C), —C(═O)—OR^(D), —C(═O)—SR^(E), —C(═O)—NR^(B1)R^(B)′, —C(═S)—R^(C′), —C(═S)—OR^(D′), —C(═S)—SR^(E′), —C(═S)—NR^(B1)R^(B2), —C(═NR^(1e))—R^(C′), —C(═NR^(1f))—OR^(D)′, —C(═NR^(1g))—SR^(E)′, —C(═NR^(1h))—NR^(B1)R^(B2), wherein R^(B1), R^(B2), R^(B2)′, R^(C), R^(C)′, R^(D), R^(D)′, R^(e), R^(E)′, R^(1e), R^(1f), R^(1g) and R^(1h) have one of the meanings given before. More preferably R¹ is —C(═S)—NR^(B1)R^(B2), wherein R^(B1) and R^(B2) have one of the meanings given before.

The radicals R^(B1) and R^(B2) are preferably selected, independently of each other, from the group consisting of hydrogen, C₁-C₃-alkyl, C₂-C₃-alkenyl, C₂-C₃-alkynyl, wherein the last three mentioned radicals may carry 1 or 2 substituents selected independently from halogen, C₁-C₃-alkoxy and C₁-C₃-haloalkoxy, C₃-C₆-cycloalkyl which is unsubstituted or may carry 1, 2 or 3 substituents R^(1e), phenyl which is unsubstituted or may carry 1, 2 or 3 substituents R^(1f), pyridyl which is unsubstituted or may carry 1, 2 or 3 substituents R^(h), wherein R^(1e), R^(1f) and R^(1h) have one of the meanings given before.

The radical R^(B2)′ is preferably selected from the group consisting of C₃-C₆-cycloalkyl which is unsubstituted or may carry 1, 2 or 3 substituents R^(1e), phenyl which is unsubstituted or may carry 1, 2 or 3 substituents R^(f), and pyridyl which is unsubstituted or may carry 1, 2 or 3 substituents R^(h), wherein R^(1e), R^(1f) and R^(1h) have one of the meanings given before.

The radical R^(C) is preferably selected from, C₁-C₃-alkyl which carries 1 or 2 radicals selected from C(═O)OH, aryloxy, arylthio or C₁-C₄-alkoxycarbonyl, wherein the three last mentioned radicals are unsubstituted or may carry 1 or 2 groups selected independently from CN, NO₂, halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl, C₁-C₃-haloalkoxy and C₃-C₆-cycloalkyl.

The radical R^(C)′ is preferably selected from the group consisting of hydrogen, C₁-C₃-alkyl, C₂-C₃-alkenyl, C₂-C₃-alkynyl, wherein the last three mentioned radicals may carry 1 or 2 substituents selected independently from halogen, C₁-C₃-alkoxy, C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio and C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl which is unsubstituted or may carry 1, 2 or 3 substituents R^(1e), phenyl which is unsubstituted or may carry 1, 2 or 3 substituents R^(1f), and pyridyl which is unsubstituted or may carry 1, 2 or 3 substituents R^(1h), wherein R^(1e), R^(1f) and R^(1h) have one of the meanings given before.

The radicals R^(D), R^(E), independently of each other, are preferably selected from the group consisting of C₂-C₃-alkenyl, C₂-C₃-alkynyl, wherein the last two mentioned radicals may carry 1, 2 or 3 substituents selected independently from halogen, C₁-C₃-alkoxy, C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio and C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl which is unsubstituted or may carry 1, 2 or 3 substituents R^(1e), phenyl which is unsubstituted or may carry 1, 2 or 3 substituents R^(1f), and pyridyl which is unsubstituted or may carry 1, 2 or 3 substituents R^(1h), wherein R^(1e), R^(1f) and R^(1h) have one of the meanings given before.

The radicals R^(D)′, R^(E)′, independently of each other, preferably have one of the preferred meanings given for R^(D), R^(E) or are selected from hydrogen or C₁-C₃-alkyl which is unsubstituted or carries 1, 2 or 3 substituents selected independently from halogen, C₁-C₃-alkoxy, C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio and C₃-C₆-cycloalkyl.

Also preferred are compounds of formula I, wherein R¹ is selected from the group consisting of C₁-C₈-alkenyl, C₁-C₈-alkynyl and C₃-C₈-cycloalkyl, which is unsubstituted or may carry 1 to 4 substituents R^(1e) as defined before.

Also preferred are compounds of formula I, wherein R¹ is selected from the group consisting of —S(═O)—R^(F), —S(═O)₂—R^(G), —S(═O)₂—NR^(B1)R^(B2)′, —P(═O)R^(H1)R^(H2), —P(═S)R^(H1)R^(H2), wherein R^(B1), R^(B2)′, R^(F), R^(G), R^(H1) and R^(H2) have one of the meanings given before.

The radicals R^(F), R^(G), R^(H1) and R^(H2), independently of each other, are preferably selected from the group consisting of hydrogen C₁-C₃-alkyl, C₂-C₃-alkenyl, C₂-C₃₋alkynyl, wherein the last three mentioned radicals may carry 1, 2 or 3 substituents selected, independently of each other, from halogen, C₁-C₃-alkoxy, C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio and C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl which is unsubstituted or may carry 1, 2 or 3 substituents R^(1e), phenyl which is unsubstituted or may carry 1, 2 or 3substituents R^(1f), and pyridyl which is unsubstituted or may carry 1, 2 or 3 substituents R^(1h), wherein R^(1e), R^(1f) and R^(1h) have one of the meanings given before.

The radical R² preferably is selected from the group consisting of hydrogen, halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy. More preferably R² is selected from hydrogen, fluoro, chloro, bromo, methyl, methoxy, difluoromethyl, trifluoromethyl, difluoromethoxy and trifluoromethoxy.

The radical R³ preferably is selected from hydrogen, halogen, C₁-C₃-alkyl and C₁-C₃-haloalkyl. More preferably R² is selected from hydrogen, fluoro, chloro, bromo, methyl, difluoromethyl and trifluoromethyl.

Also preferred are compounds of formula I, wherein R² together with R³ forms a bivalent radical selected from —O—CH₂—O—, —O—CH₂—CH₂— or —O—CF₂—O—.

The radical R⁴ preferably is selected from hydrogen, halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy. More preferably R⁴ is selected from hydrogen, fluoro, chloro, bromo, methyl, methoxy, difluoromethyl, trifluoromethyl, difluoromethoxy and trifluoromethoxy.

In one preferred embodiment of the invention R² and R³ are different from hydrogen.

In another preferred embodiment of the invention R² and R⁴ are different from hydrogen.

The radical R⁵ preferably is selected from hydrogen, halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy. More preferably R⁵ is selected from hydrogen, fluoro, chloro, bromo, methyl, methoxy, difluoromethyl, trifluoromethyl, difluoromethoxy and trifluoromethoxy.

The radical R⁶ preferably is selected from halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy. More preferably R⁶ is selected from fluoro, chloro, bromo, methyl, methoxy, difluoromethyl, trifluoromethyl, difluoromethoxy and trifluoromethoxy.

The radical R⁷ is preferably hydrogen. Likewise preferred are compounds wherein R⁷ is halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl or C₁-C₃-haloalkoxy. In particular, R⁷ is selected from hydrogen, fluoro, chloro, bromo, methyl, methoxy, difluoromethyl, trifluoromethyl, difluoromethoxy and trifluoromethoxy.

Preferably the aromatic moiety

in the formulae I, I.1. and I.2, wherein the radicals R², R³ and R⁴ have one of the meanings given before and # denotes the bonding position of formula I, is selected from aromatic moieties, wherein R² is attached at the carbon atom in ortho-position relative to the bonding position of the remainder of the compound of formula I, R³ is attached at the carbon atom next to the group CR² and in meta-position relative to the bonding position and R⁴ is attached at the carbon atom in para-position to the group CR², as shown in the following formula Ar 1:

wherein the radicals R², R³ and R⁴ have one of the meanings given before, in particular one of the preferred meanings and # each time denotes the bonding position of the remainder of formula I.

In the moiety Ar 1 the radical R² is preferably selected from the group consisting of hydrogen, halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy. More preferably, R² is selected from hydrogen, fluoro, chloro, bromo, methyl, methoxy, difluoromethyl, trifluoromethyl, difluoromethoxy and trifluoromethoxy.

In the moiety Ar 1 the radical R³ is preferably selected from hydrogen, halogen, C₁-C₃-alkyl and C₁-C₃-haloalkyl. More preferably R² is selected from hydrogen, fluoro, chloro, bromo, methyl, difluoromethyl and trifluoromethyl.

Also preferred are compounds of formula I, where in the moiety Ar 1 the radical R² together with R³ forms a bivalent radical selected from —O—CH₂—O—, —O—CH₂—CH₂— or —O—CF₂—O—.

In the moiety Ar 1 the radical R⁴ is preferably selected from hydrogen, halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy. More preferably R⁴ is selected from hydrogen, fluoro, chloro, bromo, methyl, methoxy, difluoromethyl, trifluoromethyl, difluoromethoxy and trifluoromethoxy.

In one preferred embodiment of the invention the radicals R² and R³ in the moiety Ar 1 are different from hydrogen.

In another preferred embodiment of the invention the radicals R² and R⁴ in the moiety Ar 1 are different from hydrogen.

Preferably the aromatic moiety,

wherein the radicals R⁵ and R⁶ have one of the meaning given before and # denotes the bonding position of the remainder formula I, is selected from aromatic moieties, wherein R⁵ is attached at the carbon atom in meta-position relative to the bonding position of the remainder of the compound of formula I, R⁶ is attached at the carbon atom in the remaining meta-position relative to the bonding position and R⁷ is hydrogen, as shown in the following formula Ar 2:

wherein the radicals R⁵ and R⁶ have one of the meaning given before and # denotes the bonding position of the remainder of formula I.

In the above moiety Ar 2 the radical R⁵ is preferably selected from hydrogen, halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy. More preferably R⁵ is selected from hydrogen, fluoro, chloro, bromo, methyl, methoxy, difluoromethyl, trifluoromethyl, difluoromethoxy and trifluoromethoxy.

In the above moiety Ar 2 radical R⁶ is preferably selected from halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy. More preferably R⁶ is selected from fluoro, chloro, bromo, methyl, methoxy, difluoromethyl, trifluoromethyl, difluoromethoxy and trifluoromethoxy.

A preferred embodiment of the invention relates to the compounds of formula I′

wherein A, R², R³, R⁴, R⁵ and R⁶ have one of the meanings given before.

The group of compounds of formula I′ includes compounds, wherein A is a radical of formula A.1, referred to hereinafter as compounds of formula I′.1, and compounds, wherein A is a radical of formula A.2, referred to hereinafter as compounds of formula I′.2.

A very preferred embodiment of the invention relates to the compounds of formula I′.1, as shown herein.

In formulae I′.1 and I′.2 R¹ preferably has one of the meanings which are given above as a preferred meaning. X is in particular a sulfur atom.

In a more preferred embodiment the invention relates to compounds of formula I, especially compounds of formulae I.1, I.2, I′, I′.1 and I′.2, wherein

-   R² is selected from hydrogen, halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy,     C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy, in particular hydrogen,     fluoro, chloro, bromo, methyl, methoxy, difluoromethyl,     trifluoromethyl, difluoromethoxy and trifluoromethoxy; -   R³ is selected from hydrogen, halogen, C₁-C₃-alkyl and     C₁-C₃-haloalkyl, in particular hydrogen, fluoro, chloro, bromo,     methyl, difluoromethyl and trifluoromethyl; or -   R² together with R³ forms a bivalent radical selected from     —O—CH₂—CH₂₋, —O—CH₂—O— or —O—CF₂—O—; -   R⁴ is selected from hydrogen, halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy,     C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy, in particular hydrogen,     fluoro, chloro, bromo, methyl, methoxy, difluoromethyl,     trifluoromethyl, difluoromethoxy and trifluoromethoxy; -   R⁵ is selected from hydrogen, halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy,     C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy, in particular hydrogen,     fluoro, chloro, bromo, methyl, methoxy, difluoromethyl,     trifluoromethyl, difluoromethoxy and trifluoromethoxy; and -   R⁶ is selected from halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy,     C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy, in particular fluoro, chloro,     bromo, methyl, methoxy, difluoromethyl, trifluoromethyl,     difluoromethoxy and trifluoromethoxy;

or the enantiomers, diastereomers or salts thereof.

In one preferred embodiment of the invention the radicals R² and R³ in the formulae I.1, I. 2, I′,I′.1 and I′.2 are different from hydrogen.

In another preferred embodiment of the invention the radicals R² and R⁴ in the formulae I.1, I.2, I′, I′.1 and I′.2 are different from hydrogen.

Examples of particularly preferred compounds of the general formula I are the compounds compiled in Tables A to Q below. Moreover, the meanings mentioned for the individual variables in the tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.

Table A: Examples of preferred compounds of formula I′.1 are the compounds of formula I′.1-A,

wherein R², R³, R⁴, R⁵ and R⁶ have the meanings corresponding to one line of the following table 1 (compounds I′.1-A.1 to I′.1-A.2500).

TABLE 1 R² R³ R⁴ R⁵ R⁶ A-1 F H H H F A-2 Cl H H H F A-3 CH₃ H H H F A-4 CF₃ H H H F A-5 OCH₃ H H H F A-6 F F H H F A-7 Cl F H H F A-8 CH₃ F H H F A-9 CF₃ F H H F A-10 OCH₃ F H H F A-11 F Cl H H F A-12 Cl Cl H H F A-13 CH₃ Cl H H F A-14 CF₃ Cl H H F A-15 OCH₃ Cl H H F A-16 F CH₃ H H F A-17 Cl CH₃ H H F A-18 CH₃ CH₃ H H F A-19 CF₃ CH₃ H H F A-20 OCH₃ CH₃ H H F A-21 F CF₃ H H F A-22 Cl CF₃ H H F A-23 CH₃ CF₃ H H F A-24 CF₃ CF₃ H H F A-25 OCH₃ CF₃ H H F A-26 F H F H F A-27 Cl H F H F A-28 CH₃ H F H F A-29 CF₃ H F H F A-30 OCH₃ H F H F A-31 F F F H F A-32 Cl F F H F A-33 CH₃ F F H F A-34 CF₃ F F H F A-35 OCH₃ F F H F A-36 F Cl F H F A-37 Cl Cl F H F A-38 CH₃ Cl F H F A-39 CF₃ Cl F H F A-40 OCH₃ Cl F H F A-41 F CH₃ F H F A-42 Cl CH₃ F H F A-43 CH₃ CH₃ F H F A-44 CF₃ CH₃ F H F A-45 OCH₃ CH₃ F H F A-46 F CF₃ F H F A-47 Cl CF₃ F H F A-48 CH₃ CF₃ F H F A-49 CF₃ CF₃ F H F A-50 OCH₃ CF₃ F H F A-51 F H Cl H F A-52 Cl H Cl H F A-53 CH₃ H Cl H F A-54 CF₃ H Cl H F A-55 OCH₃ H Cl H F A-56 F F Cl H F A-57 Cl F Cl H F A-58 CH₃ F Cl H F A-59 CF₃ F Cl H F A-60 OCH₃ F Cl H F A-61 F Cl Cl H F A-62 Cl Cl Cl H F A-63 CH₃ Cl Cl H F A-64 CF₃ Cl Cl H F A-65 OCH₃ Cl Cl H F A-66 F CH₃ Cl H F A-67 Cl CH₃ Cl H F A-68 CH₃ CH₃ Cl H F A-69 CF₃ CH₃ Cl H F A-70 OCH₃ CH₃ Cl H F A-71 F CF₃ Cl H F A-72 Cl CF₃ Cl H F A-73 CH₃ CF₃ Cl H F A-74 CF₃ CF₃ Cl H F A-75 OCH₃ CF₃ Cl H F A-76 F H CH₃ H F A-77 Cl H CH₃ H F A-78 CH₃ H CH₃ H F A-79 CF₃ H CH₃ H F A-80 OCH₃ H CH₃ H F A-81 F F CH₃ H F A-82 Cl F CH₃ H F A-83 CH₃ F CH₃ H F A-84 CF₃ F CH₃ H F A-85 OCH₃ F CH₃ H F A-86 F Cl CH₃ H F A-87 Cl Cl CH₃ H F A-88 CH₃ Cl CH₃ H F A-89 CF₃ Cl CH₃ H F A-90 OCH₃ Cl CH₃ H F A-91 F CH₃ CH₃ H F A-92 Cl CH₃ CH₃ H F A-93 CH₃ CH₃ CH₃ H F A-94 CF₃ CH₃ CH₃ H F A-95 OCH₃ CH₃ CH₃ H F A-96 F CF₃ CH₃ H F A-97 Cl CF₃ CH₃ H F A-98 CH₃ CF₃ CH₃ H F A-99 CF₃ CF₃ CH₃ H F A-100 OCH₃ CF₃ CH₃ H F A-101 F H CF₃ H F A-102 Cl H CF₃ H F A-103 CH₃ H CF₃ H F A-104 CF₃ H CF₃ H F A-105 OCH₃ H CF₃ H F A-106 F F CF₃ H F A-107 Cl F CF₃ H F A-108 CH₃ F CF₃ H F A-109 CF₃ F CF₃ H F A-110 OCH₃ F CF₃ H F A-111 F Cl CF₃ H F A-112 Cl Cl CF₃ H F A-113 CH₃ Cl CF₃ H F A-114 CF₃ Cl CF₃ H F A-115 OCH₃ Cl CF₃ H F A-116 F CH₃ CF₃ H F A-117 Cl CH₃ CF₃ H F A-118 CH₃ CH₃ CF₃ H F A-119 CF₃ CH₃ CF₃ H F A-120 OCH₃ CH₃ CF₃ H F A-121 F CF₃ CF₃ H F A-122 Cl CF₃ CF₃ H F A-123 CH₃ CF₃ CF₃ H F A-124 CF₃ CF₃ CF₃ H F A-125 OCH₃ CF₃ CF₃ H F A-126 F H H F F A-127 Cl H H F F A-128 CH₃ H H F F A-129 CF₃ H H F F A-130 OCH₃ H H F F A-131 F F H F F A-132 Cl F H F F A-133 CH₃ F H F F A-134 CF₃ F H F F A-135 OCH₃ F H F F A-136 F Cl H F F A-137 Cl Cl H F F A-138 CH₃ Cl H F F A-139 CF₃ Cl H F F A-140 OCH₃ Cl H F F A-141 F CH₃ H F F A-142 Cl CH₃ H F F A-143 CH₃ CH₃ H F F A-144 CF₃ CH₃ H F F A-145 OCH₃ CH₃ H F F A-146 F CF₃ H F F A-147 Cl CF₃ H F F A-148 CH₃ CF₃ H F F A-149 CF₃ CF₃ H F F A-150 OCH₃ CF₃ H F F A-151 F H F F F A-152 Cl H F F F A-153 CH₃ H F F F A-154 CF₃ H F F F A-155 OCH₃ H F F F A-156 F F F F F A-157 Cl F F F F A-158 CH₃ F F F F A-159 CF₃ F F F F A-160 OCH₃ F F F F A-161 F Cl F F F A-162 Cl Cl F F F A-163 CH₃ Cl F F F A-164 CF₃ Cl F F F A-165 OCH₃ Cl F F F A-166 F CH₃ F F F A-167 Cl CH₃ F F F A-168 CH₃ CH₃ F F F A-169 CF₃ CH₃ F F F A-170 OCH₃ CH₃ F F F A-171 F CF₃ F F F A-172 Cl CF₃ F F F A-173 CH₃ CF₃ F F F A-174 CF₃ CF₃ F F F A-175 OCH₃ CF₃ F F F A-176 F H Cl F F A-177 Cl H Cl F F A-178 CH₃ H Cl F F A-179 CF₃ H Cl F F A-180 OCH₃ H Cl F F A-181 F F Cl F F A-182 Cl F Cl F F A-183 CH₃ F Cl F F A-184 CF₃ F Cl F F A-185 OCH₃ F Cl F F A-186 F Cl Cl F F A-187 Cl Cl Cl F F A-188 CH₃ Cl Cl F F A-189 CF₃ Cl Cl F F A-190 OCH₃ Cl Cl F F A-191 F CH₃ Cl F F A-192 Cl CH₃ Cl F F A-193 CH₃ CH₃ Cl F F A-194 CF₃ CH₃ Cl F F A-195 OCH₃ CH₃ Cl F F A-196 F CF₃ Cl F F A-197 Cl CF₃ Cl F F A-198 CH₃ CF₃ Cl F F A-199 CF₃ CF₃ Cl F F A-200 OCH₃ CF₃ Cl F F A-201 F H CH₃ F F A-202 Cl H CH₃ F F A-203 CH₃ H CH₃ F F A-204 CF₃ H CH₃ F F A-205 OCH₃ H CH₃ F F A-206 F F CH₃ F F A-207 Cl F CH₃ F F A-208 CH₃ F CH₃ F F A-209 CF₃ F CH₃ F F A-210 OCH₃ F CH₃ F F A-211 F Cl CH₃ F F A-212 Cl Cl CH₃ F F A-213 CH₃ Cl CH₃ F F A-214 CF₃ Cl CH₃ F F A-215 OCH₃ Cl CH₃ F F A-216 F CH₃ CH₃ F F A-217 Cl CH₃ CH₃ F F A-218 CH₃ CH₃ CH₃ F F A-219 CF₃ CH₃ CH₃ F F A-220 OCH₃ CH₃ CH₃ F F A-221 F CF₃ CH₃ F F A-222 Cl CF₃ CH₃ F F A-223 CH₃ CF₃ CH₃ F F A-224 CF₃ CF₃ CH₃ F F A-225 OCH₃ CF₃ CH₃ F F A-226 F H CF₃ F F A-227 Cl H CF₃ F F A-228 CH₃ H CF₃ F F A-229 CF₃ H CF₃ F F A-230 OCH₃ H CF₃ F F A-231 F F CF₃ F F A-232 Cl F CF₃ F F A-233 CH₃ F CF₃ F F A-234 CF₃ F CF₃ F F A-235 OCH₃ F CF₃ F F A-236 F Cl CF₃ F F A-237 Cl Cl CF₃ F F A-238 CH₃ Cl CF₃ F F A-239 CF₃ Cl CF₃ F F A-240 OCH₃ Cl CF₃ F F A-241 F CH₃ CF₃ F F A-242 Cl CH₃ CF₃ F F A-243 CH₃ CH₃ CF₃ F F A-244 CF₃ CH₃ CF₃ F F A-245 OCH₃ CH₃ CF₃ F F A-246 F CF₃ CF₃ F F A-247 Cl CF₃ CF₃ F F A-248 CH₃ CF₃ CF₃ F F A-249 CF₃ CF₃ CF₃ F F A-250 OCH₃ CF₃ CF₃ F F A-251 F H H Cl F A-252 Cl H H Cl F A-253 CH₃ H H Cl F A-254 CF₃ H H Cl F A-255 OCH₃ H H Cl F A-256 F F H Cl F A-257 Cl F H Cl F A-258 CH₃ F H Cl F A-259 CF₃ F H Cl F A-260 OCH₃ F H Cl F A-261 F Cl H Cl F A-262 Cl Cl H Cl F A-263 CH₃ Cl H Cl F A-264 CF₃ Cl H Cl F A-265 OCH₃ Cl H Cl F A-266 F CH₃ H Cl F A-267 Cl CH₃ H Cl F A-268 CH₃ CH₃ H Cl F A-269 CF₃ CH₃ H Cl F A-270 OCH₃ CH₃ H Cl F A-271 F CF₃ H Cl F A-272 Cl CF₃ H Cl F A-273 CH₃ CF₃ H Cl F A-274 CF₃ CF₃ H Cl F A-275 OCH₃ CF₃ H Cl F A-276 F H F Cl F A-277 Cl H F Cl F A-278 CH₃ H F Cl F A-279 CF₃ H F Cl F A-280 OCH₃ H F Cl F A-281 F F F Cl F A-282 Cl F F Cl F A-283 CH₃ F F Cl F A-284 CF₃ F F Cl F A-285 OCH₃ F F Cl F A-286 F Cl F Cl F A-287 Cl Cl F Cl F A-288 CH₃ Cl F Cl F A-289 CF₃ Cl F Cl F A-290 OCH₃ Cl F Cl F A-291 F CH₃ F Cl F A-292 Cl CH₃ F Cl F A-293 CH₃ CH₃ F Cl F A-294 CF₃ CH₃ F Cl F A-295 OCH₃ CH₃ F Cl F A-296 F CF₃ F Cl F A-297 Cl CF₃ F Cl F A-298 CH₃ CF₃ F Cl F A-299 CF₃ CF₃ F Cl F A-300 OCH₃ CF₃ F Cl F A-301 F H Cl Cl F A-302 Cl H Cl Cl F A-303 CH₃ H Cl Cl F A-304 CF₃ H Cl Cl F A-305 OCH₃ H Cl Cl F A-306 F F Cl Cl F A-307 Cl F Cl Cl F A-308 CH₃ F Cl Cl F A-309 CF₃ F Cl Cl F A-310 OCH₃ F Cl Cl F A-311 F Cl Cl Cl F A-312 Cl Cl Cl Cl F A-391 F CH₃ H CH₃ F A-392 Cl CH₃ H CH₃ F A-393 CH₃ CH₃ H CH₃ F A-394 CF₃ CH₃ H CH₃ F A-395 OCH₃ CH₃ H CH₃ F A-396 F CF₃ H CH₃ F A-397 Cl CF₃ H CH₃ F A-398 CH₃ CF₃ H CH₃ F A-399 CF₃ CF₃ H CH₃ F A-400 OCH₃ CF₃ H CH₃ F A-401 F H F CH₃ F A-402 Cl H F CH₃ F A-403 CH₃ H F CH₃ F A-404 CF₃ H F CH₃ F A-405 OCH₃ H F CH₃ F A-406 F F F CH₃ F A-407 Cl F F CH₃ F A-408 CH₃ F F CH₃ F A-409 CF₃ F F CH₃ F A-410 OCH₃ F F CH₃ F A-411 F Cl F CH₃ F A-412 Cl Cl F CH₃ F A-413 CH₃ Cl F CH₃ F A-414 CF₃ Cl F CH₃ F A-415 OCH₃ Cl F CH₃ F A-416 F CH₃ F CH₃ F A-417 Cl CH₃ F CH₃ F A-418 CH₃ CH₃ F CH₃ F A-419 CF₃ CH₃ F CH₃ F A-420 OCH₃ CH₃ F CH₃ F A-421 F CF₃ F CH₃ F A-422 Cl CF₃ F CH₃ F A-423 CH₃ CF₃ F CH₃ F A-424 CF₃ CF₃ F CH₃ F A-425 OCH₃ CF₃ F CH₃ F A-426 F H Cl CH₃ F A-427 Cl H Cl CH₃ F A-428 CH₃ H Cl CH₃ F A-429 CF₃ H Cl CH₃ F A-430 OCH₃ H Cl CH₃ F A-431 F F Cl CH₃ F A-432 Cl F Cl CH₃ F A-433 CH₃ F Cl CH₃ F A-434 CF₃ F Cl CH₃ F A-435 OCH₃ F Cl CH₃ F A-436 F Cl Cl CH₃ F A-437 Cl Cl Cl CH₃ F A-438 CH₃ Cl Cl CH₃ F A-439 CF₃ Cl Cl CH₃ F A-440 OCH₃ Cl Cl CH₃ F A-441 F CH₃ Cl CH₃ F A-442 Cl CH₃ Cl CH₃ F A-443 CH₃ CH₃ Cl CH₃ F A-444 CF₃ CH₃ Cl CH₃ F A-445 OCH₃ CH₃ Cl CH₃ F A-446 F CF₃ Cl CH₃ F A-447 Cl CF₃ Cl CH₃ F A-448 CH₃ CF₃ Cl CH₃ F A-449 CF₃ CF₃ Cl CH₃ F A-450 OCH₃ CF₃ Cl CH₃ F A-451 F H CH₃ CH₃ F A-452 Cl H CH₃ CH₃ F A-453 CH₃ H CH₃ CH₃ F A-454 CF₃ H CH₃ CH₃ F A-455 OCH₃ H CH₃ CH₃ F A-456 F F CH₃ CH₃ F A-457 Cl F CH₃ CH₃ F A-458 CH₃ F CH₃ CH₃ F A-459 CF₃ F CH₃ CH₃ F A-460 OCH₃ F CH₃ CH₃ F A-461 F Cl CH₃ CH₃ F A-462 Cl Cl CH₃ CH₃ F A-463 CH₃ Cl CH₃ CH₃ F A-464 CF₃ Cl CH₃ CH₃ F A-465 OCH₃ Cl CH₃ CH₃ F A-466 F CH₃ CH₃ CH₃ F A-467 Cl CH₃ CH₃ CH₃ F A-468 CH₃ CH₃ CH₃ CH₃ F A-469 CF₃ CH₃ CH₃ CH₃ F A-470 OCH₃ CH₃ CH₃ CH₃ F A-471 F CF₃ CH₃ CH₃ F A-472 Cl CF₃ CH₃ CH₃ F A-473 CH₃ CF₃ CH₃ CH₃ F A-474 CF₃ CF₃ CH₃ CH₃ F A-475 OCH₃ CF₃ CH₃ CH₃ F A-476 F H CF₃ CH₃ F A-477 Cl H CF₃ CH₃ F A-478 CH₃ H CF₃ CH₃ F A-479 CF₃ H CF₃ CH₃ F A-480 OCH₃ H CF₃ CH₃ F A-481 F F CF₃ CH₃ F A-482 Cl F CF₃ CH₃ F A-483 CH₃ F CF₃ CH₃ F A-484 CF₃ F CF₃ CH₃ F A-485 OCH₃ F CF₃ CH₃ F A-486 F Cl CF₃ CH₃ F A-487 Cl Cl CF₃ CH₃ F A-488 CH₃ Cl CF₃ CH₃ F A-489 CF₃ Cl CF₃ CH₃ F A-490 OCH₃ Cl CF₃ CH₃ F A-491 F CH₃ CF₃ CH₃ F A-492 Cl CH₃ CF₃ CH₃ F A-493 CH₃ CH₃ CF₃ CH₃ F A-494 CF₃ CH₃ CF₃ CH₃ F A-495 OCH₃ CH₃ CF₃ CH₃ F A-496 F CF₃ CF₃ CH₃ F A-497 Cl CF₃ CF₃ CH₃ F A-498 CH₃ CF₃ CF₃ CH₃ F A-499 CF₃ CF₃ CF₃ CH₃ F A-500 OCH₃ CF₃ CF₃ CH₃ F A-501 F H H CF₃ F A-502 Cl H H CF₃ F A-503 CH₃ H H CF₃ F A-504 CF₃ H H CF₃ F A-505 OCH₃ H H CF₃ F A-506 F F H CF₃ F A-507 Cl F H CF₃ F A-508 CH₃ F H CF₃ F A-509 CF₃ F H CF₃ F A-510 OCH₃ F H CF₃ F A-511 F Cl H CF₃ F A-512 Cl Cl H CF₃ F A-513 CH₃ Cl H CF₃ F A-514 CF₃ Cl H CF₃ F A-515 OCH₃ Cl H CF₃ F A-516 F CH₃ H CF₃ F A-517 Cl CH₃ H CF₃ F A-518 CH₃ CH₃ H CF₃ F A-519 CF₃ CH₃ H CF₃ F A-520 OCH₃ CH₃ H CF₃ F A-521 F CF₃ H CF₃ F A-522 Cl CF₃ H CF₃ F A-523 CH₃ CF₃ H CF₃ F A-524 CF₃ CF₃ H CF₃ F A-525 OCH₃ CF₃ H CF₃ F A-526 F H F CF₃ F A-527 Cl H F CF₃ F A-528 CH₃ H F CF₃ F A-529 CF₃ H F CF₃ F A-530 OCH₃ H F CF₃ F A-531 F F F CF₃ F A-532 Cl F F CF₃ F A-533 CH₃ F F CF₃ F A-534 CF₃ F F CF₃ F A-535 OCH₃ F F CF₃ F A-536 F Cl F CF₃ F A-537 Cl Cl F CF₃ F A-538 CH₃ Cl F CF₃ F A-539 CF₃ Cl F CF₃ F A-540 OCH₃ Cl F CF₃ F A-541 F CH₃ F CF₃ F A-542 Cl CH₃ F CF₃ F A-543 CH₃ CH₃ F CF₃ F A-544 CF₃ CH₃ F CF₃ F A-545 OCH₃ CH₃ F CF₃ F A-546 F CF₃ F CF₃ F A-547 Cl CF₃ F CF₃ F A-548 CH₃ CF₃ F CF₃ F A-549 CF₃ CF₃ F CF₃ F A-550 OCH₃ CF₃ F CF₃ F A-551 F H Cl CF₃ F A-552 Cl H Cl CF₃ F A-553 CH₃ H Cl CF₃ F A-554 CF₃ H Cl CF₃ F A-555 OCH₃ H Cl CF₃ F A-556 F F Cl CF₃ F A-557 Cl F Cl CF₃ F A-558 CH₃ F Cl CF₃ F A-559 CF₃ F Cl CF₃ F A-560 OCH₃ F Cl CF₃ F A-561 F Cl Cl CF₃ F A-562 Cl Cl Cl CF₃ F A-563 CH₃ Cl Cl CF₃ F A-564 CF₃ Cl Cl CF₃ F A-565 OCH₃ Cl Cl CF₃ F A-566 F CH₃ Cl CF₃ F A-567 Cl CH₃ Cl CF₃ F A-568 CH₃ CH₃ Cl CF₃ F A-569 CF₃ CH₃ Cl CF₃ F A-570 OCH₃ CH₃ Cl CF₃ F A-571 F CF₃ Cl CF₃ F A-572 Cl CF₃ Cl CF₃ F A-573 CH₃ CF₃ Cl CF₃ F A-574 CF₃ CF₃ Cl CF₃ F A-575 OCH₃ CF₃ Cl CF₃ F A-576 F H CH₃ CF₃ F A-577 Cl H CH₃ CF₃ F A-578 CH₃ H CH₃ CF₃ F A-579 CF₃ H CH₃ CF₃ F A-580 OCH₃ H CH₃ CF₃ F A-581 F F CH₃ CF₃ F A-582 Cl F CH₃ CF₃ F A-583 CH₃ F CH₃ CF₃ F A-584 CF₃ F CH₃ CF₃ F A-585 OCH₃ F CH₃ CF₃ F A-586 F Cl CH₃ CF₃ F A-587 Cl Cl CH₃ CF₃ F A-588 CH₃ Cl CH₃ CF₃ F A-589 CF₃ Cl CH₃ CF₃ F A-590 OCH₃ Cl CH₃ CF₃ F A-591 F CH₃ CH₃ CF₃ F A-592 Cl CH₃ CH₃ CF₃ F A-593 CH₃ CH₃ CH₃ CF₃ F A-594 CF₃ CH₃ CH₃ CF₃ F A-595 OCH₃ CH₃ CH₃ CF₃ F A-596 F CF₃ CH₃ CF₃ F A-597 Cl CF₃ CH₃ CF₃ F A-598 CH₃ CF₃ CH₃ CF₃ F A-599 CF₃ CF₃ CH₃ CF₃ F A-600 OCH₃ CF₃ CH₃ CF₃ F A-601 F H CF₃ CF₃ F A-602 Cl H CF₃ CF₃ F A-603 CH₃ H CF₃ CF₃ F A-604 CF₃ H CF₃ CF₃ F A-605 OCH₃ H CF₃ CF₃ F A-606 F F CF₃ CF₃ F A-607 Cl F CF₃ CF₃ F A-608 CH₃ F CF₃ CF₃ F A-609 CF₃ F CF₃ CF₃ F A-610 OCH₃ F CF₃ CF₃ F A-611 F Cl CF₃ CF₃ F A-612 Cl Cl CF₃ CF₃ F A-613 CH₃ Cl CF₃ CF₃ F A-614 CF₃ Cl CF₃ CF₃ F A-615 OCH₃ Cl CF₃ CF₃ F A-616 F CH₃ CF₃ CF₃ F A-617 Cl CH₃ CF₃ CF₃ F A-618 CH₃ CH₃ CF₃ CF₃ F A-619 CF₃ CH₃ CF₃ CF₃ F A-620 OCH₃ CH₃ CF₃ CF₃ F A-621 F CF₃ CF₃ CF₃ F A-622 Cl CF₃ CF₃ CF₃ F A-623 CH₃ CF₃ CF₃ CF₃ F A-624 CF₃ CF₃ CF₃ CF₃ F A-625 OCH₃ CF₃ CF₃ CF₃ F A-626 F H H H Cl A-627 Cl H H H Cl A-628 CH₃ H H H Cl A-629 CF₃ H H H Cl A-630 OCH₃ H H H Cl A-631 F F H H Cl A-632 Cl F H H Cl A-633 CH₃ F H H Cl A-634 CF₃ F H H Cl A-635 OCH₃ F H H Cl A-636 F Cl H H Cl A-637 Cl Cl H H Cl A-638 CH₃ Cl H H Cl A-639 CF₃ Cl H H Cl A-640 OCH₃ Cl H H Cl A-641 F CH₃ H H Cl A-642 Cl CH₃ H H Cl A-643 CH₃ CH₃ H H Cl A-644 CF₃ CH₃ H H Cl A-645 OCH₃ CH₃ H H Cl A-646 F CF₃ H H Cl A-647 Cl CF₃ H H Cl A-648 CH₃ CF₃ H H Cl A-649 CF₃ CF₃ H H Cl A-650 OCH₃ CF₃ H H Cl A-651 F H F H Cl A-652 Cl H F H Cl A-653 CH₃ H F H Cl A-654 CF₃ H F H Cl A-655 OCH₃ H F H Cl A-656 F F F H Cl A-657 Cl F F H Cl A-658 CH₃ F F H Cl A-659 CF₃ F F H Cl A-660 OCH₃ F F H Cl A-661 F Cl F H Cl A-662 Cl Cl F H Cl A-663 CH₃ Cl F H Cl A-664 CF₃ Cl F H Cl A-665 OCH₃ Cl F H Cl A-666 F CH₃ F H Cl A-667 Cl CH₃ F H Cl A-668 CH₃ CH₃ F H Cl A-669 CF₃ CH₃ F H Cl A-670 OCH₃ CH₃ F H Cl A-671 F CF₃ F H Cl A-672 Cl CF₃ F H Cl A-673 CH₃ CF₃ F H Cl A-674 CF₃ CF₃ F H Cl A-675 OCH₃ CF₃ F H Cl A-676 F H Cl H Cl A-677 Cl H Cl H Cl A-678 CH₃ H Cl H Cl A-679 CF₃ H Cl H Cl A-680 OCH₃ H Cl H Cl A-681 F F Cl H Cl A-682 Cl F Cl H Cl A-683 CH₃ F Cl H Cl A-684 CF₃ F Cl H Cl A-685 OCH₃ F Cl H Cl A-686 F Cl Cl H Cl A-687 Cl Cl Cl H Cl A-688 CH₃ Cl Cl H Cl A-689 CF₃ Cl Cl H Cl A-690 OCH₃ Cl Cl H Cl A-691 F CH₃ Cl H Cl A-692 Cl CH₃ Cl H Cl A-693 CH₃ CH₃ Cl H Cl A-694 CF₃ CH₃ Cl H Cl A-695 OCH₃ CH₃ Cl H Cl A-696 F CF₃ Cl H Cl A-697 Cl CF₃ Cl H Cl A-698 CH₃ CF₃ Cl H Cl A-699 CF₃ CF₃ Cl H Cl A-700 OCH₃ CF₃ Cl H Cl A-701 F H CH₃ H Cl A-702 Cl H CH₃ H Cl A-703 CH₃ H CH₃ H Cl A-704 CF₃ H CH₃ H Cl A-705 OCH₃ H CH₃ H Cl A-706 F F CH₃ H Cl A-707 Cl F CH₃ H Cl A-708 CH₃ F CH₃ H Cl A-709 CF₃ F CH₃ H Cl A-710 OCH₃ F CH₃ H Cl A-711 F Cl CH₃ H Cl A-712 Cl Cl CH₃ H Cl A-713 CH₃ Cl CH₃ H Cl A-714 CF₃ Cl CH₃ H Cl A-715 OCH₃ Cl CH₃ H Cl A-716 F CH₃ CH₃ H Cl A-717 Cl CH₃ CH₃ H Cl A-718 CH₃ CH₃ CH₃ H Cl A-719 CF₃ CH₃ CH₃ H Cl A-720 OCH₃ CH₃ CH₃ H Cl A-721 F CF₃ CH₃ H Cl A-722 Cl CF₃ CH₃ H Cl A-723 CH₃ CF₃ CH₃ H Cl A-724 CF₃ CF₃ CH₃ H Cl A-725 OCH₃ CF₃ CH₃ H Cl A-726 F H CF₃ H Cl A-727 Cl H CF₃ H Cl A-728 CH₃ H CF₃ H Cl A-729 CF₃ H CF₃ H Cl A-730 OCH₃ H CF₃ H Cl A-731 F F CF₃ H Cl A-732 Cl F CF₃ H Cl A-733 CH₃ F CF₃ H Cl A-734 CF₃ F CF₃ H Cl A-735 OCH₃ F CF₃ H Cl A-736 F Cl CF₃ H Cl A-737 Cl Cl CF₃ H Cl A-738 CH₃ Cl CF₃ H Cl A-739 CF₃ Cl CF₃ H Cl A-740 OCH₃ Cl CF₃ H Cl A-741 F CH₃ CF₃ H Cl A-742 Cl CH₃ CF₃ H Cl A-743 CH₃ CH₃ CF₃ H Cl A-744 CF₃ CH₃ CF₃ H Cl A-745 OCH₃ CH₃ CF₃ H Cl A-746 F CF₃ CF₃ H Cl A-747 Cl CF₃ CF₃ H Cl A-748 CH₃ CF₃ CF₃ H Cl A-749 CF₃ CF₃ CF₃ H Cl A-750 OCH₃ CF₃ CF₃ H Cl A-751 F H H F Cl A-752 Cl H H F Cl A-753 CH₃ H H F Cl A-754 CF₃ H H F Cl A-755 OCH₃ H H F Cl A-756 F F H F Cl A-757 Cl F H F Cl A-758 CH₃ F H F Cl A-759 CF₃ F H F Cl A-760 OCH₃ F H F Cl A-761 F Cl H F Cl A-762 Cl Cl H F Cl A-763 CH₃ Cl H F Cl A-764 CF₃ Cl H F Cl A-765 OCH₃ Cl H F Cl A-766 F CH₃ H F Cl A-767 Cl CH₃ H F Cl A-768 CH₃ CH₃ H F Cl A-769 CF₃ CH₃ H F Cl A-770 OCH₃ CH₃ H F Cl A-771 F CF₃ H F Cl A-772 Cl CF₃ H F Cl A-773 CH₃ CF₃ H F Cl A-774 CF₃ CF₃ H F Cl A-775 OCH₃ CF₃ H F Cl A-776 F H F F Cl A-777 Cl H F F Cl A-778 CH₃ H F F Cl A-779 CF₃ H F F Cl A-780 OCH₃ H F F Cl A-781 F F F F Cl A-782 Cl F F F Cl A-783 CH₃ F F F Cl A-784 CF₃ F F F Cl A-785 OCH₃ F F F Cl A-786 F Cl F F Cl A-787 Cl Cl F F Cl A-788 CH₃ Cl F F Cl A-789 CF₃ Cl F F Cl A-790 OCH₃ Cl F F Cl A-791 F CH₃ F F Cl A-792 Cl CH₃ F F Cl A-793 CH₃ CH₃ F F Cl A-794 CF₃ CH₃ F F Cl A-795 OCH₃ CH₃ F F Cl A-796 F CF₃ F F Cl A-797 Cl CF₃ F F Cl A-798 CH₃ CF₃ F F Cl A-799 CF₃ CF₃ F F Cl A-800 OCH₃ CF₃ F F Cl A-801 F H Cl F Cl A-802 Cl H Cl F Cl A-803 CH₃ H Cl F Cl A-804 CF₃ H Cl F Cl A-805 OCH₃ H Cl F Cl A-806 F F Cl F Cl A-807 Cl F Cl F Cl A-808 CH₃ F Cl F Cl A-809 CF₃ F Cl F Cl A-810 OCH₃ F Cl F Cl A-811 F Cl Cl F Cl A-812 Cl Cl Cl F Cl A-813 CH₃ Cl Cl F Cl A-814 CF₃ Cl Cl F Cl A-815 OCH₃ Cl Cl F Cl A-816 F CH₃ Cl F Cl A-817 Cl CH₃ Cl F Cl A-818 CH₃ CH₃ Cl F Cl A-819 CF₃ CH₃ Cl F Cl A-820 OCH₃ CH₃ Cl F Cl A-821 F CF₃ Cl F Cl A-822 Cl CF₃ Cl F Cl A-823 CH₃ CF₃ Cl F Cl A-824 CF₃ CF₃ Cl F Cl A-825 OCH₃ CF₃ Cl F Cl A-826 F H CH₃ F Cl A-827 Cl H CH₃ F Cl A-828 CH₃ H CH₃ F Cl A-829 CF₃ H CH₃ F Cl A-830 OCH₃ H CH₃ F Cl A-831 F F CH₃ F Cl A-832 Cl F CH₃ F Cl A-833 CH₃ F CH₃ F Cl A-834 CF₃ F CH₃ F Cl A-835 OCH₃ F CH₃ F Cl A-836 F Cl CH₃ F Cl A-837 Cl Cl CH₃ F Cl A-838 CH₃ Cl CH₃ F Cl A-839 CF₃ Cl CH₃ F Cl A-840 OCH₃ Cl CH₃ F Cl A-841 F CH₃ CH₃ F Cl A-842 Cl CH₃ CH₃ F Cl A-843 CH₃ CH₃ CH₃ F Cl A-844 CF₃ CH₃ CH₃ F Cl A-845 OCH₃ CH₃ CH₃ F Cl A-846 F CF₃ CH₃ F Cl A-847 Cl CF₃ CH₃ F Cl A-848 CH₃ CF₃ CH₃ F Cl A-849 CF₃ CF₃ CH₃ F Cl A-850 OCH₃ CF₃ CH₃ F Cl A-851 F H CF₃ F Cl A-852 Cl H CF₃ F Cl A-853 CH₃ H CF₃ F Cl A-854 CF₃ H CF₃ F Cl A-855 OCH₃ H CF₃ F Cl A-856 F F CF₃ F Cl A-857 Cl F CF₃ F Cl A-858 CH₃ F CF₃ F Cl A-859 CF₃ F CF₃ F Cl A-860 OCH₃ F CF₃ F Cl A-861 F Cl CF₃ F Cl A-862 Cl Cl CF₃ F Cl A-863 CH₃ Cl CF₃ F Cl A-864 CF₃ Cl CF₃ F Cl A-865 OCH₃ Cl CF₃ F Cl A-866 F CH₃ CF₃ F Cl A-867 Cl CH₃ CF₃ F Cl A-868 CH₃ CH₃ CF₃ F Cl A-869 CF₃ CH₃ CF₃ F Cl A-870 OCH₃ CH₃ CF₃ F Cl A-871 F CF₃ CF₃ F Cl A-872 Cl CF₃ CF₃ F Cl A-873 CH₃ CF₃ CF₃ F Cl A-874 CF₃ CF₃ CF₃ F Cl A-875 OCH₃ CF₃ CF₃ F Cl A-876 F H H Cl Cl A-877 Cl H H Cl Cl A-878 CH₃ H H Cl Cl A-879 CF₃ H H Cl Cl A-880 OCH₃ H H Cl Cl A-881 F F H Cl Cl A-882 Cl F H Cl Cl A-883 CH₃ F H Cl Cl A-884 CF₃ F H Cl Cl A-885 OCH₃ F H Cl Cl A-886 F Cl H Cl Cl A-887 Cl Cl H Cl Cl A-888 CH₃ Cl H Cl Cl A-889 CF₃ Cl H Cl Cl A-890 OCH₃ Cl H Cl Cl A-891 F CH₃ H Cl Cl A-892 Cl CH₃ H Cl Cl A-893 CH₃ CH₃ H Cl Cl A-894 CF₃ CH₃ H Cl Cl A-895 OCH₃ CH₃ H Cl Cl A-896 F CF₃ H Cl Cl A-897 Cl CF₃ H Cl Cl A-898 CH₃ CF₃ H Cl Cl A-899 CF₃ CF₃ H Cl Cl A-900 OCH₃ CF₃ H Cl Cl A-901 F H F Cl Cl A-902 Cl H F Cl Cl A-903 CH₃ H F Cl Cl A-904 CF₃ H F Cl Cl A-905 OCH₃ H F Cl Cl A-906 F F F Cl Cl A-907 Cl F F Cl Cl A-908 CH₃ F F Cl Cl A-909 CF₃ F F Cl Cl A-910 OCH₃ F F Cl Cl A-911 F Cl F Cl Cl A-912 Cl Cl F Cl Cl A-913 CH₃ Cl F Cl Cl A-914 CF₃ Cl F Cl Cl A-915 OCH₃ Cl F Cl Cl A-916 F CH₃ F Cl Cl A-917 Cl CH₃ F Cl Cl A-918 CH₃ CH₃ F Cl Cl A-919 CF₃ CH₃ F Cl Cl A-920 OCH₃ CH₃ F Cl Cl A-921 F CF₃ F Cl Cl A-922 Cl CF₃ F Cl Cl A-923 CH₃ CF₃ F Cl Cl A-924 CF₃ CF₃ F Cl Cl A-925 OCH₃ CF₃ F Cl Cl A-926 F H Cl Cl Cl A-927 Cl H Cl Cl Cl A-928 CH₃ H Cl Cl Cl A-929 CF₃ H Cl Cl Cl A-930 OCH₃ H Cl Cl Cl A-931 F F Cl Cl Cl A-932 Cl F Cl Cl Cl A-933 CH₃ F Cl Cl Cl A-934 CF₃ F Cl Cl Cl A-935 OCH₃ F Cl Cl Cl A-936 F Cl Cl Cl Cl A-937 Cl Cl Cl Cl Cl A-938 CH₃ Cl Cl Cl Cl A-939 CF₃ Cl Cl Cl Cl A-940 OCH₃ Cl Cl Cl Cl A-941 F CH₃ Cl Cl Cl A-942 Cl CH₃ Cl Cl Cl A-943 CH₃ CH₃ Cl Cl Cl A-944 CF₃ CH₃ Cl Cl Cl A-945 OCH₃ CH₃ Cl Cl Cl A-946 F CF₃ Cl Cl Cl A-947 Cl CF₃ Cl Cl Cl A-948 CH₃ CF₃ Cl Cl Cl A-949 CF₃ CF₃ Cl Cl Cl A-950 OCH₃ CF₃ Cl Cl Cl A-951 F H CH₃ Cl Cl A-952 Cl H CH₃ Cl Cl A-953 CH₃ H CH₃ Cl Cl A-954 CF₃ H CH₃ Cl Cl A-955 OCH₃ H CH₃ Cl Cl A-956 F F CH₃ Cl Cl A-957 Cl F CH₃ Cl Cl A-958 CH₃ F CH₃ Cl Cl A-959 CF₃ F CH₃ Cl Cl A-960 OCH₃ F CH₃ Cl Cl A-961 F Cl CH₃ Cl Cl A-962 Cl Cl CH₃ Cl Cl A-963 CH₃ Cl CH₃ Cl Cl A-964 CF₃ Cl CH₃ Cl Cl A-965 OCH₃ Cl CH₃ Cl Cl A-966 F CH₃ CH₃ Cl Cl A-967 Cl CH₃ CH₃ Cl Cl A-968 CH₃ CH₃ CH₃ Cl Cl A-969 CF₃ CH₃ CH₃ Cl Cl A-970 OCH₃ CH₃ CH₃ Cl Cl A-971 F CF₃ CH₃ Cl Cl A-972 Cl CF₃ CH₃ Cl Cl A-973 CH₃ CF₃ CH₃ Cl Cl A-974 CF₃ CF₃ CH₃ Cl Cl A-975 OCH₃ CF₃ CH₃ Cl Cl A-976 F H CF₃ Cl Cl A-977 Cl H CF₃ Cl Cl A-978 CH₃ H CF₃ Cl Cl A-979 CF₃ H CF₃ Cl Cl A-980 OCH₃ H CF₃ Cl Cl A-981 F F CF₃ Cl Cl A-982 Cl F CF₃ Cl Cl A-983 CH₃ F CF₃ Cl Cl A-984 CF₃ F CF₃ Cl Cl A-985 OCH₃ F CF₃ Cl Cl A-986 F Cl CF₃ Cl Cl A-987 Cl Cl CF₃ Cl Cl A-988 CH₃ Cl CF₃ Cl Cl A-989 CF₃ Cl CF₃ Cl Cl A-990 OCH₃ Cl CF₃ Cl Cl A-991 F CH₃ CF₃ Cl Cl A-992 Cl CH₃ CF₃ Cl Cl A-993 CH₃ CH₃ CF₃ Cl Cl A-994 CF₃ CH₃ CF₃ Cl Cl A-995 OCH₃ CH₃ CF₃ Cl Cl A-996 F CF₃ CF₃ Cl Cl A-997 Cl CF₃ CF₃ Cl Cl A-998 CH₃ CF₃ CF₃ Cl Cl A-999 CF₃ CF₃ CF₃ Cl Cl A-1000 OCH₃ CF₃ CF₃ Cl Cl A-1001 F H H CH₃ Cl A-1002 Cl H H CH₃ Cl A-1003 CH₃ H H CH₃ Cl A-1004 CF₃ H H CH₃ Cl A-1005 OCH₃ H H CH₃ Cl A-1006 F F H CH₃ Cl A-1007 Cl F H CH₃ Cl A-1008 CH₃ F H CH₃ Cl A-1009 CF₃ F H CH₃ Cl A-1010 OCH₃ F H CH₃ Cl A-1011 F Cl H CH₃ Cl A-1012 Cl Cl H CH₃ Cl A-1013 CH₃ Cl H CH₃ Cl A-1014 CF₃ Cl H CH₃ Cl A-1015 OCH₃ Cl H CH₃ Cl A-1016 F CH₃ H CH₃ Cl A-1017 Cl CH₃ H CH₃ Cl A-1018 CH₃ CH₃ H CH₃ Cl A-1019 CF₃ CH₃ H CH₃ Cl A-1020 OCH₃ CH₃ H CH₃ Cl A-1021 F CF₃ H CH₃ Cl A-1022 Cl CF₃ H CH₃ Cl A-1023 CH₃ CF₃ H CH₃ Cl A-1024 CF₃ CF₃ H CH₃ Cl A-1025 OCH₃ CF₃ H CH₃ Cl A-1026 F H F CH₃ Cl A-1027 Cl H F CH₃ Cl A-1028 CH₃ H F CH₃ Cl A-1029 CF₃ H F CH₃ Cl A-1030 OCH₃ H F CH₃ Cl A-1031 F F F CH₃ Cl A-1032 Cl F F CH₃ Cl A-1033 CH₃ F F CH₃ Cl A-1034 CF₃ F F CH₃ Cl A-1035 OCH₃ F F CH₃ Cl A-1036 F Cl F CH₃ Cl A-1037 Cl Cl F CH₃ Cl A-1038 CH₃ Cl F CH₃ Cl A-1039 CF₃ Cl F CH₃ Cl A-1040 OCH₃ Cl F CH₃ Cl A-1041 F CH₃ F CH₃ Cl A-1042 Cl CH₃ F CH₃ Cl A-1043 CH₃ CH₃ F CH₃ Cl A-1044 CF₃ CH₃ F CH₃ Cl A-1045 OCH₃ CH₃ F CH₃ Cl A-1046 F CF₃ F CH₃ Cl A-1047 Cl CF₃ F CH₃ Cl A-1048 CH₃ CF₃ F CH₃ Cl A-1049 CF₃ CF₃ F CH₃ Cl A-1050 OCH₃ CF₃ F CH₃ Cl A-1051 F H Cl CH₃ Cl A-1052 Cl H Cl CH₃ Cl A-1053 CH₃ H Cl CH₃ Cl A-1054 CF₃ H Cl CH₃ Cl A-1055 OCH₃ H Cl CH₃ Cl A-1056 F F Cl CH₃ Cl A-1057 Cl F Cl CH₃ Cl A-1058 CH₃ F Cl CH₃ Cl A-1059 CF₃ F Cl CH₃ Cl A-1060 OCH₃ F Cl CH₃ Cl A-1061 F Cl Cl CH₃ Cl A-1062 Cl Cl Cl CH₃ Cl A-1063 CH₃ Cl Cl CH₃ Cl A-1064 CF₃ Cl Cl CH₃ Cl A-1065 OCH₃ Cl Cl CH₃ Cl A-1066 F CH₃ Cl CH₃ Cl A-1067 Cl CH₃ Cl CH₃ Cl A-1068 CH₃ CH₃ Cl CH₃ Cl A-1069 CF₃ CH₃ Cl CH₃ Cl A-1070 OCH₃ CH₃ Cl CH₃ Cl A-1071 F CF₃ Cl CH₃ Cl A-1072 Cl CF₃ Cl CH₃ Cl A-1073 CH₃ CF₃ Cl CH₃ Cl A-1074 CF₃ CF₃ Cl CH₃ Cl A-1075 OCH₃ CF₃ Cl CH₃ Cl A-1076 F H CH₃ CH₃ Cl A-1077 Cl H CH₃ CH₃ Cl A-1078 CH₃ H CH₃ CH₃ Cl A-1079 CF₃ H CH₃ CH₃ Cl A-1080 OCH₃ H CH₃ CH₃ Cl A-1081 F F CH₃ CH₃ Cl A-1082 Cl F CH₃ CH₃ Cl A-1083 CH₃ F CH₃ CH₃ Cl A-1084 CF₃ F CH₃ CH₃ Cl A-1085 OCH₃ F CH₃ CH₃ Cl A-1086 F Cl CH₃ CH₃ Cl A-1087 Cl Cl CH₃ CH₃ Cl A-1088 CH₃ Cl CH₃ CH₃ Cl A-1089 CF₃ Cl CH₃ CH₃ Cl A-1090 OCH₃ Cl CH₃ CH₃ Cl A-1091 F CH₃ CH₃ CH₃ Cl A-1092 Cl CH₃ CH₃ CH₃ Cl A-1093 CH₃ CH₃ CH₃ CH₃ Cl A-1094 CF₃ CH₃ CH₃ CH₃ Cl A-1095 OCH₃ CH₃ CH₃ CH₃ Cl A-1096 F CF₃ CH₃ CH₃ Cl A-1097 Cl CF₃ CH₃ CH₃ Cl A-1098 CH₃ CF₃ CH₃ CH₃ Cl A-1099 CF₃ CF₃ CH₃ CH₃ Cl A-1100 OCH₃ CF₃ CH₃ CH₃ Cl A-1101 F H CF₃ CH₃ Cl A-1102 Cl H CF₃ CH₃ Cl A-1103 CH₃ H CF₃ CH₃ Cl A-1104 CF₃ H CF₃ CH₃ Cl A-1105 OCH₃ H CF₃ CH₃ Cl A-1106 F F CF₃ CH₃ Cl A-1107 Cl F CF₃ CH₃ Cl A-1108 CH₃ F CF₃ CH₃ Cl A-1109 CF₃ F CF₃ CH₃ Cl A-1110 OCH₃ F CF₃ CH₃ Cl A-1111 F Cl CF₃ CH₃ Cl A-1112 Cl Cl CF₃ CH₃ Cl A-1113 CH₃ Cl CF₃ CH₃ Cl A-1114 CF₃ Cl CF₃ CH₃ Cl A-1115 OCH₃ Cl CF₃ CH₃ Cl A-1116 F CH₃ CF₃ CH₃ Cl A-1117 Cl CH₃ CF₃ CH₃ Cl A-1118 CH₃ CH₃ CF₃ CH₃ Cl A-1119 CF₃ CH₃ CF₃ CH₃ Cl A-1120 OCH₃ CH₃ CF₃ CH₃ Cl A-1121 F CF₃ CF₃ CH₃ Cl A-1122 Cl CF₃ CF₃ CH₃ Cl A-1123 CH₃ CF₃ CF₃ CH₃ Cl A-1124 CF₃ CF₃ CF₃ CH₃ Cl A-1125 OCH₃ CF₃ CF₃ CH₃ Cl A-1126 F H H CF₃ Cl A-1127 Cl H H CF₃ Cl A-1128 CH₃ H H CF₃ Cl A-1129 CF₃ H H CF₃ Cl A-1130 OCH₃ H H CF₃ Cl A-1131 F F H CF₃ Cl A-1132 Cl F H CF₃ Cl A-1133 CH₃ F H CF₃ Cl A-1134 CF₃ F H CF₃ Cl A-1135 OCH₃ F H CF₃ Cl A-1136 F Cl H CF₃ Cl A-1137 Cl Cl H CF₃ Cl A-1138 CH₃ Cl H CF₃ Cl A-1139 CF₃ Cl H CF₃ Cl A-1140 OCH₃ Cl H CF₃ Cl A-1141 F CH₃ H CF₃ Cl A-1142 Cl CH₃ H CF₃ Cl A-1143 CH₃ CH₃ H CF₃ Cl A-1144 CF₃ CH₃ H CF₃ Cl A-1145 OCH₃ CH₃ H CF₃ Cl A-1146 F CF₃ H CF₃ Cl A-1147 Cl CF₃ H CF₃ Cl A-1148 CH₃ CF₃ H CF₃ Cl A-1149 CF₃ CF₃ H CF₃ Cl A-1150 OCH₃ CF₃ H CF₃ Cl A-1151 F H F CF₃ Cl A-1152 Cl H F CF₃ Cl A-1153 CH₃ H F CF₃ Cl A-1154 CF₃ H F CF₃ Cl A-1155 OCH₃ H F CF₃ Cl A-1156 F F F CF₃ Cl A-1157 Cl F F CF₃ Cl A-1158 CH₃ F F CF₃ Cl A-1159 CF₃ F F CF₃ Cl A-1160 OCH₃ F F CF₃ Cl A-1161 F Cl F CF₃ Cl A-1162 Cl Cl F CF₃ Cl A-1163 CH₃ Cl F CF₃ Cl A-1164 CF₃ Cl F CF₃ Cl A-1165 OCH₃ Cl F CF₃ Cl A-1166 F CH₃ F CF₃ Cl A-1167 Cl CH₃ F CF₃ Cl A-1168 CH₃ CH₃ F CF₃ Cl A-1169 CF₃ CH₃ F CF₃ Cl A-1170 OCH₃ CH₃ F CF₃ Cl A-1171 F CF₃ F CF₃ Cl A-1172 Cl CF₃ F CF₃ Cl A-1173 CH₃ CF₃ F CF₃ Cl A-1174 CF₃ CF₃ F CF₃ Cl A-1175 OCH₃ CF₃ F CF₃ Cl A-1176 F H Cl CF₃ Cl A-1177 Cl H Cl CF₃ Cl A-1178 CH₃ H Cl CF₃ Cl A-1179 CF₃ H Cl CF₃ Cl A-1180 OCH₃ H Cl CF₃ Cl A-1181 F F Cl CF₃ Cl A-1182 Cl F Cl CF₃ Cl A-1183 CH₃ F Cl CF₃ Cl A-1184 CF₃ F Cl CF₃ Cl A-1185 OCH₃ F Cl CF₃ Cl A-1186 F Cl Cl CF₃ Cl A-1187 Cl Cl Cl CF₃ Cl A-1188 CH₃ Cl Cl CF₃ Cl A-1189 CF₃ Cl Cl CF₃ Cl A-1190 OCH₃ Cl Cl CF₃ Cl A-1191 F CH₃ Cl CF₃ Cl A-1192 Cl CH₃ Cl CF₃ Cl A-1193 CH₃ CH₃ Cl CF₃ Cl A-1194 CF₃ CH₃ Cl CF₃ Cl A-1195 OCH₃ CH₃ Cl CF₃ Cl A-1196 F CF₃ Cl CF₃ Cl A-1197 Cl CF₃ Cl CF₃ Cl A-1198 CH₃ CF₃ Cl CF₃ Cl A-1199 CF₃ CF₃ Cl CF₃ Cl A-1200 OCH₃ CF₃ Cl CF₃ Cl A-1201 F H CH₃ CF₃ Cl A-1202 Cl H CH₃ CF₃ Cl A-1203 CH₃ H CH₃ CF₃ Cl A-1204 CF₃ H CH₃ CF₃ Cl A-1205 OCH₃ H CH₃ CF₃ Cl A-1206 F F CH₃ CF₃ Cl A-1207 Cl F CH₃ CF₃ Cl A-1208 CH₃ F CH₃ CF₃ Cl A-1209 CF₃ F CH₃ CF₃ Cl A-1210 OCH₃ F CH₃ CF₃ Cl A-1211 F Cl CH₃ CF₃ Cl A-1212 Cl Cl CH₃ CF₃ Cl A-1213 CH₃ Cl CH₃ CF₃ Cl A-1214 CF₃ Cl CH₃ CF₃ Cl A-1215 OCH₃ Cl CH₃ CF₃ Cl A-1216 F CH₃ CH₃ CF₃ Cl A-1217 Cl CH₃ CH₃ CF₃ Cl A-1218 CH₃ CH₃ CH₃ CF₃ Cl A-1219 CF₃ CH₃ CH₃ CF₃ Cl A-1220 OCH₃ CH₃ CH₃ CF₃ Cl A-1221 F CF₃ CH₃ CF₃ Cl A-1222 Cl CF₃ CH₃ CF₃ Cl A-1223 CH₃ CF₃ CH₃ CF₃ Cl A-1224 CF₃ CF₃ CH₃ CF₃ Cl A-1225 OCH₃ CF₃ CH₃ CF₃ Cl A-1226 F H CF₃ CF₃ Cl A-1227 Cl H CF₃ CF₃ Cl A-1228 CH₃ H CF₃ CF₃ Cl A-1229 CF₃ H CF₃ CF₃ Cl A-1230 OCH₃ H CF₃ CF₃ Cl A-1231 F F CF₃ CF₃ Cl A-1232 Cl F CF₃ CF₃ Cl A-1233 CH₃ F CF₃ CF₃ Cl A-1234 CF₃ F CF₃ CF₃ Cl A-1235 OCH₃ F CF₃ CF₃ Cl A-1236 F Cl CF₃ CF₃ Cl A-1237 Cl Cl CF₃ CF₃ Cl A-1238 CH₃ Cl CF₃ CF₃ Cl A-1239 CF₃ Cl CF₃ CF₃ Cl A-1240 OCH₃ Cl CF₃ CF₃ Cl A-1241 F CH₃ CF₃ CF₃ Cl A-1242 Cl CH₃ CF₃ CF₃ Cl A-1243 CH₃ CH₃ CF₃ CF₃ Cl A-1244 CF₃ CH₃ CF₃ CF₃ Cl A-1245 OCH₃ CH₃ CF₃ CF₃ Cl A-1246 F CF₃ CF₃ CF₃ Cl A-1247 Cl CF₃ CF₃ CF₃ Cl A-1248 CH₃ CF₃ CF₃ CF₃ Cl A-1249 CF₃ CF₃ CF₃ CF₃ Cl A-1250 OCH₃ CF₃ CF₃ CF₃ Cl A-1251 F H H H CH₃ A-1252 Cl H H H CH₃ A-1253 CH₃ H H H CH₃ A-1254 CF₃ H H H CH₃ A-1255 OCH₃ H H H CH₃ A-1256 F F H H CH₃ A-1257 Cl F H H CH₃ A-1258 CH₃ F H H CH₃ A-1259 CF₃ F H H CH₃ A-1260 OCH₃ F H H CH₃ A-1261 F Cl H H CH₃ A-1262 Cl Cl H H CH₃ A-1263 CH₃ Cl H H CH₃ A-1264 CF₃ Cl H H CH₃ A-1265 OCH₃ Cl H H CH₃ A-1266 F CH₃ H H CH₃ A-1267 Cl CH₃ H H CH₃ A-1268 CH₃ CH₃ H H CH₃ A-1269 CF₃ CH₃ H H CH₃ A-1270 OCH₃ CH₃ H H CH₃ A-1271 F CF₃ H H CH₃ A-1272 Cl CF₃ H H CH₃ A-1273 CH₃ CF₃ H H CH₃ A-1274 CF₃ CF₃ H H CH₃ A-1275 OCH₃ CF₃ H H CH₃ A-1276 F H F H CH₃ A-1277 Cl H F H CH₃ A-1278 CH₃ H F H CH₃ A-1279 CF₃ H F H CH₃ A-1280 OCH₃ H F H CH₃ A-1281 F F F H CH₃ A-1282 Cl F F H CH₃ A-1283 CH₃ F F H CH₃ A-1284 CF₃ F F H CH₃ A-1285 OCH₃ F F H CH₃ A-1286 F Cl F H CH₃ A-1287 Cl Cl F H CH₃ A-1288 CH₃ Cl F H CH₃ A-1289 CF₃ Cl F H CH₃ A-1290 OCH₃ Cl F H CH₃ A-1291 F CH₃ F H CH₃ A-1292 Cl CH₃ F H CH₃ A-1293 CH₃ CH₃ F H CH₃ A-1294 CF₃ CH₃ F H CH₃ A-1295 OCH₃ CH₃ F H CH₃ A-1296 F CF₃ F H CH₃ A-1297 Cl CF₃ F H CH₃ A-1298 CH₃ CF₃ F H CH₃ A-1299 CF₃ CF₃ F H CH₃ A-1300 OCH₃ CF₃ F H CH₃ A-1301 F H Cl H CH₃ A-1302 Cl H Cl H CH₃ A-1303 CH₃ H Cl H CH₃ A-1304 CF₃ H Cl H CH₃ A-1305 OCH₃ H Cl H CH₃ A-1306 F F Cl H CH₃ A-1307 Cl F Cl H CH₃ A-1308 CH₃ F Cl H CH₃ A-1309 CF₃ F Cl H CH₃ A-1310 OCH₃ F Cl H CH₃ A-1311 F Cl Cl H CH₃ A-1312 Cl Cl Cl H CH₃ A-1313 CH₃ Cl Cl H CH₃ A-1314 CF₃ Cl Cl H CH₃ A-1315 OCH₃ Cl Cl H CH₃ A-1316 F CH₃ Cl H CH₃ A-1317 Cl CH₃ Cl H CH₃ A-1318 CH₃ CH₃ Cl H CH₃ A-1319 CF₃ CH₃ Cl H CH₃ A-1320 OCH₃ CH₃ Cl H CH₃ A-1321 F CF₃ Cl H CH₃ A-1322 Cl CF₃ Cl H CH₃ A-1323 CH₃ CF₃ Cl H CH₃ A-1324 CF₃ CF₃ Cl H CH₃ A-1325 OCH₃ CF₃ Cl H CH₃ A-1326 F H CH₃ H CH₃ A-1327 Cl H CH₃ H CH₃ A-1328 CH₃ H CH₃ H CH₃ A-1329 CF₃ H CH₃ H CH₃ A-1330 OCH₃ H CH₃ H CH₃ A-1331 F F CH₃ H CH₃ A-1332 Cl F CH₃ H CH₃ A-1333 CH₃ F CH₃ H CH₃ A-1334 CF₃ F CH₃ H CH₃ A-1335 OCH₃ F CH₃ H CH₃ A-1336 F Cl CH₃ H CH₃ A-1337 Cl Cl CH₃ H CH₃ A-1338 CH₃ Cl CH₃ H CH₃ A-1339 CF₃ Cl CH₃ H CH₃ A-1340 OCH₃ Cl CH₃ H CH₃ A-1341 F CH₃ CH₃ H CH₃ A-1342 Cl CH₃ CH₃ H CH₃ A-1343 CH₃ CH₃ CH₃ H CH₃ A-1344 CF₃ CH₃ CH₃ H CH₃ A-1345 OCH₃ CH₃ CH₃ H CH₃ A-1346 F CF₃ CH₃ H CH₃ A-1347 Cl CF₃ CH₃ H CH₃ A-1348 CH₃ CF₃ CH₃ H CH₃ A-1349 CF₃ CF₃ CH₃ H CH₃ A-1350 OCH₃ CF₃ CH₃ H CH₃ A-1351 F H CF₃ H CH₃ A-1352 Cl H CF₃ H CH₃ A-1353 CH₃ H CF₃ H CH₃ A-1354 CF₃ H CF₃ H CH₃ A-1355 OCH₃ H CF₃ H CH₃ A-1356 F F CF₃ H CH₃ A-1357 Cl F CF₃ H CH₃ A-1358 CH₃ F CF₃ H CH₃ A-1359 CF₃ F CF₃ H CH₃ A-1360 OCH₃ F CF₃ H CH₃ A-1361 F Cl CF₃ H CH₃ A-1362 Cl Cl CF₃ H CH₃ A-1363 CH₃ Cl CF₃ H CH₃ A-1364 CF₃ Cl CF₃ H CH₃ A-1365 OCH₃ Cl CF₃ H CH₃ A-1366 F CH₃ CF₃ H CH₃ A-1367 Cl CH₃ CF₃ H CH₃ A-1368 CH₃ CH₃ CF₃ H CH₃ A-1369 CF₃ CH₃ CF₃ H CH₃ A-1370 OCH₃ CH₃ CF₃ H CH₃ A-1371 F CF₃ CF₃ H CH₃ A-1372 Cl CF₃ CF₃ H CH₃ A-1373 CH₃ CF₃ CF₃ H CH₃ A-1374 CF₃ CF₃ CF₃ H CH₃ A-1375 OCH₃ CF₃ CF₃ H CH₃ A-1376 F H H F CH₃ A-1377 Cl H H F CH₃ A-1378 CH₃ H H F CH₃ A-1379 CF₃ H H F CH₃ A-1380 OCH₃ H H F CH₃ A-1381 F F H F CH₃ A-1382 Cl F H F CH₃ A-1383 CH₃ F H F CH₃ A-1384 CF₃ F H F CH₃ A-1385 OCH₃ F H F CH₃ A-1386 F Cl H F CH₃ A-1387 Cl Cl H F CH₃ A-1388 CH₃ Cl H F CH₃ A-1389 CF₃ Cl H F CH₃ A-1390 OCH₃ Cl H F CH₃ A-1391 F CH₃ H F CH₃ A-1392 Cl CH₃ H F CH₃ A-1393 CH₃ CH₃ H F CH₃ A-1394 CF₃ CH₃ H F CH₃ A-1395 OCH₃ CH₃ H F CH₃ A-1396 F CF₃ H F CH₃ A-1397 Cl CF₃ H F CH₃ A-1398 CH₃ CF₃ H F CH₃ A-1399 CF₃ CF₃ H F CH₃ A-1400 OCH₃ CF₃ H F CH₃ A-1401 F H F F CH₃ A-1402 Cl H F F CH₃ A-1403 CH₃ H F F CH₃ A-1404 CF₃ H F F CH₃ A-1405 OCH₃ H F F CH₃ A-1406 F F F F CH₃ A-1407 Cl F F F CH₃ A-1408 CH₃ F F F CH₃ A-1409 CF₃ F F F CH₃ A-1410 OCH₃ F F F CH₃ A-1411 F Cl F F CH₃ A-1412 Cl Cl F F CH₃ A-1413 CH₃ Cl F F CH₃ A-1414 CF₃ Cl F F CH₃ A-1415 OCH₃ Cl F F CH₃ A-1416 F CH₃ F F CH₃ A-1417 Cl CH₃ F F CH₃ A-1418 CH₃ CH₃ F F CH₃ A-1419 CF₃ CH₃ F F CH₃ A-1420 OCH₃ CH₃ F F CH₃ A-1421 F CF₃ F F CH₃ A-1422 Cl CF₃ F F CH₃ A-1423 CH₃ CF₃ F F CH₃ A-1424 CF₃ CF₃ F F CH₃ A-1425 OCH₃ CF₃ F F CH₃ A-1426 F H Cl F CH₃ A-1427 Cl H Cl F CH₃ A-1428 CH₃ H Cl F CH₃ A-1429 CF₃ H Cl F CH₃ A-1430 OCH₃ H Cl F CH₃ A-1431 F F Cl F CH₃ A-1432 Cl F Cl F CH₃ A-1433 CH₃ F Cl F CH₃ A-1434 CF₃ F Cl F CH₃ A-1435 OCH₃ F Cl F CH₃ A-1436 F Cl Cl F CH₃ A-1437 Cl Cl Cl F CH₃ A-1438 CH₃ Cl Cl F CH₃ A-1439 CF₃ Cl Cl F CH₃ A-1440 OCH₃ Cl Cl F CH₃ A-1441 F CH₃ Cl F CH₃ A-1442 Cl CH₃ Cl F CH₃ A-1443 CH₃ CH₃ Cl F CH₃ A-1444 CF₃ CH₃ Cl F CH₃ A-1445 OCH₃ CH₃ Cl F CH₃ A-1446 F CF₃ Cl F CH₃ A-1447 Cl CF₃ Cl F CH₃ A-1448 CH₃ CF₃ Cl F CH₃ A-1449 CF₃ CF₃ Cl F CH₃ A-1450 OCH₃ CF₃ Cl F CH₃ A-1451 F H CH₃ F CH₃ A-1452 Cl H CH₃ F CH₃ A-1453 CH₃ H CH₃ F CH₃ A-1454 CF₃ H CH₃ F CH₃ A-1455 OCH₃ H CH₃ F CH₃ A-1456 F F CH₃ F CH₃ A-1457 Cl F CH₃ F CH₃ A-1458 CH₃ F CH₃ F CH₃ A-1459 CF₃ F CH₃ F CH₃ A-1460 OCH₃ F CH₃ F CH₃ A-1461 F CI CH₃ F CH₃ A-1462 Cl Cl CH₃ F CH₃ A-1463 CH₃ Cl CH₃ F CH₃ A-1464 CF₃ Cl CH₃ F CH₃ A-1465 OCH₃ Cl CH₃ F CH₃ A-1466 F CH₃ CH₃ F CH₃ A-1467 Cl CH₃ CH₃ F CH₃ A-1468 CH₃ CH₃ CH₃ F CH₃ A-1469 CF₃ CH₃ CH₃ F CH₃ A-1470 OCH₃ CH₃ CH₃ F CH₃ A-1471 F CF₃ CH₃ F CH₃ A-1472 Cl CF₃ CH₃ F CH₃ A-1473 CH₃ CF₃ CH₃ F CH₃ A-1474 CF₃ CF₃ CH₃ F CH₃ A-1475 OCH₃ CF₃ CH₃ F CH₃ A-1476 F H CF₃ F CH₃ A-1477 Cl H CF₃ F CH₃ A-1478 CH₃ H CF₃ F CH₃ A-1479 CF₃ H CF₃ F CH₃ A-1480 OCH₃ H CF₃ F CH₃ A-1481 F F CF₃ F CH₃ A-1482 Cl F CF₃ F CH₃ A-1483 CH₃ F CF₃ F CH₃ A-1484 CF₃ F CF₃ F CH₃ A-1485 OCH₃ F CF₃ F CH₃ A-1486 F Cl CF₃ F CH₃ A-1487 Cl Cl CF₃ F CH₃ A-1488 CH₃ Cl CF₃ F CH₃ A-1489 CF₃ Cl CF₃ F CH₃ A-1490 OCH₃ Cl CF₃ F CH₃ A-1491 F CH₃ CF₃ F CH₃ A-1492 Cl CH₃ CF₃ F CH₃ A-1493 CH₃ CH₃ CF₃ F CH₃ A-1494 CF₃ CH₃ CF₃ F CH₃ A-1495 OCH₃ CH₃ CF₃ F CH₃ A-1496 F CF₃ CF₃ F CH₃ A-1497 Cl CF₃ CF₃ F CH₃ A-1498 CH₃ CF₃ CF₃ F CH₃ A-1499 CF₃ CF₃ CF₃ F CH₃ A-1500 OCH₃ CF₃ CF₃ F CH₃ A-1501 F H H Cl CH₃ A-1502 Cl H H Cl CH₃ A-1503 CH₃ H H Cl CH₃ A-1504 CF₃ H H Cl CH₃ A-1505 OCH₃ H H Cl CH₃ A-1506 F F H Cl CH₃ A-1507 Cl F H Cl CH₃ A-1508 CH₃ F H Cl CH₃ A-1509 CF₃ F H Cl CH₃ A-1510 OCH₃ F H Cl CH₃ A-1511 F Cl H Cl CH₃ A-1512 Cl Cl H Cl CH₃ A-1513 CH₃ Cl H Cl CH₃ A-1514 CF₃ Cl H Cl CH₃ A-1515 OCH₃ Cl H Cl CH₃ A-1516 F CH₃ H Cl CH₃ A-1517 Cl CH₃ H Cl CH₃ A-1518 CH₃ CH₃ H Cl CH₃ A-1519 CF₃ CH₃ H Cl CH₃ A-1520 OCH₃ CH₃ H Cl CH₃ A-1521 F CF₃ H Cl CH₃ A-1522 Cl CF₃ H Cl CH₃ A-1523 CH₃ CF₃ H Cl CH₃ A-1524 CF₃ CF₃ H Cl CH₃ A-1525 OCH₃ CF₃ H Cl CH₃ A-1526 F H F Cl CH₃ A-1527 Cl H F Cl CH₃ A-1528 CH₃ H F Cl CH₃ A-1529 CF₃ H F Cl CH₃ A-1530 OCH₃ H F Cl CH₃ A-1531 F F F Cl CH₃ A-1532 Cl F F Cl CH₃ A-1533 CH₃ F F Cl CH₃ A-1534 CF₃ F F Cl CH₃ A-1535 OCH₃ F F Cl CH₃ A-1536 F Cl F Cl CH₃ A-1537 Cl Cl F Cl CH₃ A-1538 CH₃ Cl F Cl CH₃ A-1539 CF₃ Cl F Cl CH₃ A-1540 OCH₃ Cl F Cl CH₃ A-1541 F CH₃ F Cl CH₃ A-1542 Cl CH₃ F Cl CH₃ A-1543 CH₃ CH₃ F Cl CH₃ A-1544 CF₃ CH₃ F Cl CH₃ A-1545 OCH₃ CH₃ F Cl CH₃ A-1546 F CF₃ F Cl CH₃ A-1547 Cl CF₃ F Cl CH₃ A-1548 CH₃ CF₃ F Cl CH₃ A-1549 CF₃ CF₃ F Cl CH₃ A-1550 OCH₃ CF₃ F Cl CH₃ A-1551 F H Cl Cl CH₃ A-1552 Cl H Cl Cl CH₃ A-1553 CH₃ H Cl Cl CH₃ A-1554 CF₃ H Cl Cl CH₃ A-1555 OCH₃ H Cl Cl CH₃ A-1556 F F Cl Cl CH₃ A-1557 Cl F Cl Cl CH₃ A-1558 CH₃ F Cl Cl CH₃ A-1559 CF₃ F Cl Cl CH₃ A-1560 OCH₃ F Cl Cl CH₃ A-1561 F Cl Cl Cl CH₃ A-1562 Cl Cl Cl Cl CH₃ A-1563 CH₃ Cl Cl Cl CH₃ A-1564 CF₃ Cl Cl Cl CH₃ A-1565 OCH₃ Cl Cl Cl CH₃ A-1566 F CH₃ Cl Cl CH₃ A-1567 Cl CH₃ Cl Cl CH₃ A-1568 CH₃ CH₃ Cl Cl CH₃ A-1569 CF₃ CH₃ Cl Cl CH₃ A-1570 OCH₃ CH₃ Cl Cl CH₃ A-1571 F CF₃ Cl Cl CH₃ A-1572 Cl CF₃ Cl Cl CH₃ A-1573 CH₃ CF₃ Cl Cl CH₃ A-1574 CF₃ CF₃ Cl Cl CH₃ A-1575 OCH₃ CF₃ Cl Cl CH₃ A-1576 F H CH₃ Cl CH₃ A-1577 Cl H CH₃ Cl CH₃ A-1578 CH₃ H CH₃ Cl CH₃ A-1579 CF₃ H CH₃ Cl CH₃ A-1580 OCH₃ H CH₃ Cl CH₃ A-1581 F F CH₃ Cl CH₃ A-1582 Cl F CH₃ Cl CH₃ A-1583 CH₃ F CH₃ Cl CH₃ A-1584 CF₃ F CH₃ Cl CH₃ A-1585 OCH₃ F CH₃ Cl CH₃ A-1586 F Cl CH₃ Cl CH₃ A-1587 Cl Cl CH₃ Cl CH₃ A-1588 CH₃ Cl CH₃ Cl CH₃ A-1589 CF₃ Cl CH₃ Cl CH₃ A-1590 OCH₃ Cl CH₃ Cl CH₃ A-1591 F CH₃ CH₃ Cl CH₃ A-1592 Cl CH₃ CH₃ Cl CH₃ A-1593 CH₃ CH₃ CH₃ Cl CH₃ A-1594 CF₃ CH₃ CH₃ Cl CH₃ A-1595 OCH₃ CH₃ CH₃ Cl CH₃ A-1596 F CF₃ CH₃ Cl CH₃ A-1597 Cl CF₃ CH₃ Cl CH₃ A-1598 CH₃ CF₃ CH₃ Cl CH₃ A-1599 CF₃ CF₃ CH₃ Cl CH₃ A-1600 OCH₃ CF₃ CH₃ Cl CH₃ A-1601 F H CF₃ Cl CH₃ A-1602 Cl H CF₃ Cl CH₃ A-1603 CH₃ H CF₃ Cl CH₃ A-1604 CF₃ H CF₃ Cl CH₃ A-1605 OCH₃ H CF₃ Cl CH₃ A-1606 F F CF₃ Cl CH₃ A-1607 Cl F CF₃ Cl CH₃ A-1608 CH₃ F CF₃ Cl CH₃ A-1609 CF₃ F CF₃ Cl CH₃ A-1610 OCH₃ F CF₃ Cl CH₃ A-1611 F Cl CF₃ Cl CH₃ A-1612 Cl Cl CF₃ Cl CH₃ A-1613 CH₃ Cl CF₃ Cl CH₃ A-1614 CF₃ Cl CF₃ Cl CH₃ A-1615 OCH₃ Cl CF₃ Cl CH₃ A-1616 F CH₃ CF₃ Cl CH₃ A-1617 Cl CH₃ CF₃ Cl CH₃ A-1618 CH₃ CH₃ CF₃ Cl CH₃ A-1619 CF₃ CH₃ CF₃ Cl CH₃ A-1620 OCH₃ CH₃ CF₃ Cl CH₃ A-1621 F CF₃ CF₃ Cl CH₃ A-1622 Cl CF₃ CF₃ Cl CH₃ A-1623 CH₃ CF₃ CF₃ Cl CH₃ A-1624 CF₃ CF₃ CF₃ Cl CH₃ A-1625 OCH₃ CF₃ CF₃ Cl CH₃ A-1626 F H H CH₃ CH₃ A-1627 Cl H H CH₃ CH₃ A-1628 CH₃ H H CH₃ CH₃ A-1629 CF₃ H H CH₃ CH₃ A-1630 OCH₃ H H CH₃ CH₃ A-1631 F F H CH₃ CH₃ A-1632 Cl F H CH₃ CH₃ A-1633 CH₃ F H CH₃ CH₃ A-1634 CF₃ F H CH₃ CH₃ A-1635 OCH₃ F H CH₃ CH₃ A-1636 F Cl H CH₃ CH₃ A-1637 Cl Cl H CH₃ CH₃ A-1638 CH₃ Cl H CH₃ CH₃ A-1639 CF₃ Cl H CH₃ CH₃ A-1640 OCH₃ Cl H CH₃ CH₃ A-1641 F CH₃ H CH₃ CH₃ A-1642 Cl CH₃ H CH₃ CH₃ A-1643 CH₃ CH₃ H CH₃ CH₃ A-1644 CF₃ CH₃ H CH₃ CH₃ A-1645 OCH₃ CH₃ H CH₃ CH₃ A-1646 F CF₃ H CH₃ CH₃ A-1647 Cl CF₃ H CH₃ CH₃ A-1648 CH₃ CF₃ H CH₃ CH₃ A-1649 CF₃ CF₃ H CH₃ CH₃ A-1650 OCH₃ CF₃ H CH₃ CH₃ A-1651 F H F CH₃ CH₃ A-1652 Cl H F CH₃ CH₃ A-1653 CH₃ H F CH₃ CH₃ A-1654 CF₃ H F CH₃ CH₃ A-1655 OCH₃ H F CH₃ CH₃ A-1656 F F F CH₃ CH₃ A-1657 Cl F F CH₃ CH₃ A-1658 CH₃ F F CH₃ CH₃ A-1659 CF₃ F F CH₃ CH₃ A-1660 OCH₃ F F CH₃ CH₃ A-1661 F Cl F CH₃ CH₃ A-1662 Cl Cl F CH₃ CH₃ A-1663 CH₃ Cl F CH₃ CH₃ A-1664 CF₃ Cl F CH₃ CH₃ A-1665 OCH₃ Cl F CH₃ CH₃ A-1666 F CH₃ F CH₃ CH₃ A-1667 Cl CH₃ F CH₃ CH₃ A-1668 CH₃ CH₃ F CH₃ CH₃ A-1669 CF₃ CH₃ F CH₃ CH₃ A-1670 OCH₃ CH₃ F CH₃ CH₃ A-1671 F CF₃ F CH₃ CH₃ A-1672 Cl CF₃ F CH₃ CH₃ A-1673 CH₃ CF₃ F CH₃ CH₃ A-1674 CF₃ CF₃ F CH₃ CH₃ A-1675 OCH₃ CF₃ F CH₃ CH₃ A-1676 F H Cl CH₃ CH₃ A-1677 Cl H Cl CH₃ CH₃ A-1678 CH₃ H Cl CH₃ CH₃ A-1679 CF₃ H Cl CH₃ CH₃ A-1680 OCH₃ H Cl CH₃ CH₃ A-1681 F F Cl CH₃ CH₃ A-1682 Cl F Cl CH₃ CH₃ A-1683 CH₃ F Cl CH₃ CH₃ A-1684 CF₃ F Cl CH₃ CH₃ A-1685 OCH₃ F Cl CH₃ CH₃ A-1686 F Cl Cl CH₃ CH₃ A-1687 Cl Cl Cl CH₃ CH₃ A-1688 CH₃ Cl Cl CH₃ CH₃ A-1689 CF₃ Cl Cl CH₃ CH₃ A-1690 OCH₃ Cl Cl CH₃ CH₃ A-1691 F CH₃ Cl CH₃ CH₃ A-1692 Cl CH₃ Cl CH₃ CH₃ A-1693 CH₃ CH₃ Cl CH₃ CH₃ A-1694 CF₃ CH₃ Cl CH₃ CH₃ A-1695 OCH₃ CH₃ Cl CH₃ CH₃ A-1696 F CF₃ Cl CH₃ CH₃ A-1697 Cl CF₃ Cl CH₃ CH₃ A-1698 CH₃ CF₃ Cl CH₃ CH₃ A-1699 CF₃ CF₃ Cl CH₃ CH₃ A-1700 OCH₃ CF₃ Cl CH₃ CH₃ A-1701 F H CH₃ CH₃ CH₃ A-1702 Cl H CH₃ CH₃ CH₃ A-1703 CH₃ H CH₃ CH₃ CH₃ A-1704 CF₃ H CH₃ CH₃ CH₃ A-1705 OCH₃ H CH₃ CH₃ CH₃ A-1706 F F CH₃ CH₃ CH₃ A-1707 Cl F CH₃ CH₃ CH₃ A-1708 CH₃ F CH₃ CH₃ CH₃ A-1709 CF₃ F CH₃ CH₃ CH₃ A-1710 OCH₃ F CH₃ CH₃ CH₃ A-1711 F Cl CH₃ CH₃ CH₃ A-1712 Cl Cl CH₃ CH₃ CH₃ A-1713 CH₃ Cl CH₃ CH₃ CH₃ A-1714 CF₃ Cl CH₃ CH₃ CH₃ A-1715 OCH₃ Cl CH₃ CH₃ CH₃ A-1716 F CH₃ CH₃ CH₃ CH₃ A-1717 Cl CH₃ CH₃ CH₃ CH₃ A-1718 CH₃ CH₃ CH₃ CH₃ CH₃ A-1719 CF₃ CH₃ CH₃ CH₃ CH₃ A-1720 OCH₃ CH₃ CH₃ CH₃ CH₃ A-1721 F CF₃ CH₃ CH₃ CH₃ A-1722 Cl CF₃ CH₃ CH₃ CH₃ A-1723 CH₃ CF₃ CH₃ CH₃ CH₃ A-1724 CF₃ CF₃ CH₃ CH₃ CH₃ A-1725 OCH₃ CF₃ CH₃ CH₃ CH₃ A-1726 F H CF₃ CH₃ CH₃ A-1727 Cl H CF₃ CH₃ CH₃ A-1728 CH₃ H CF₃ CH₃ CH₃ A-1729 CF₃ H CF₃ CH₃ CH₃ A-1730 OCH₃ H CF₃ CH₃ CH₃ A-1731 F F CF₃ CH₃ CH₃ A-1732 Cl F CF₃ CH₃ CH₃ A-1733 CH₃ F CF₃ CH₃ CH₃ A-1734 CF₃ F CF₃ CH₃ CH₃ A-1735 OCH₃ F CF₃ CH₃ CH₃ A-1736 F Cl CF₃ CH₃ CH₃ A-1737 Cl Cl CF₃ CH₃ CH₃ A-1738 CH₃ Cl CF₃ CH₃ CH₃ A-1739 CF₃ Cl CF₃ CH₃ CH₃ A-1740 OCH₃ Cl CF₃ CH₃ CH₃ A-1741 F CH₃ CF₃ CH₃ CH₃ A-1742 Cl CH₃ CF₃ CH₃ CH₃ A-1743 CH₃ CH₃ CF₃ CH₃ CH₃ A-1744 CF₃ CH₃ CF₃ CH₃ CH₃ A-1745 OCH₃ CH₃ CF₃ CH₃ CH₃ A-1746 F CF₃ CF₃ CH₃ CH₃ A-1747 Cl CF₃ CF₃ CH₃ CH₃ A-1748 CH₃ CF₃ CF₃ CH₃ CH₃ A-1749 CF₃ CF₃ CF₃ CH₃ CH₃ A-1750 OCH₃ CF₃ CF₃ CH₃ CH₃ A-1751 F H H CF₃ CH₃ A-1752 Cl H H CF₃ CH₃ A-1753 CH₃ H H CF₃ CH₃ A-1754 CF₃ H H CF₃ CH₃ A-1755 OCH₃ H H CF₃ CH₃ A-1756 F F H CF₃ CH₃ A-1757 Cl F H CF₃ CH₃ A-1758 CH₃ F H CF₃ CH₃ A-1759 CF₃ F H CF₃ CH₃ A-1760 OCH₃ F H CF₃ CH₃ A-1761 F Cl H CF₃ CH₃ A-1762 Cl Cl H CF₃ CH₃ A-1763 CH₃ Cl H CF₃ CH₃ A-1764 CF₃ Cl H CF₃ CH₃ A-1765 OCH₃ Cl H CF₃ CH₃ A-1766 F CH₃ H CF₃ CH₃ A-1767 Cl CH₃ H CF₃ CH₃ A-1768 CH₃ CH₃ H CF₃ CH₃ A-1769 CF₃ CH₃ H CF₃ CH₃ A-1770 OCH₃ CH₃ H CF₃ CH₃ A-1771 F CF₃ H CF₃ CH₃ A-1772 Cl CF₃ H CF₃ CH₃ A-1773 CH₃ CF₃ H CF₃ CH₃ A-1774 CF₃ CF₃ H CF₃ CH₃ A-1775 OCH₃ CF₃ H CF₃ CH₃ A-1776 F H F CF₃ CH₃ A-1777 Cl H F CF₃ CH₃ A-1778 CH₃ H F CF₃ CH₃ A-1779 CF₃ H F CF₃ CH₃ A-1780 OCH₃ H F CF₃ CH₃ A-1781 F F F CF₃ CH₃ A-1782 Cl F F CF₃ CH₃ A-1783 CH₃ F F CF₃ CH₃ A-1784 CF₃ F F CF₃ CH₃ A-1785 OCH₃ F F CF₃ CH₃ A-1786 F Cl F CF₃ CH₃ A-1787 Cl Cl F CF₃ CH₃ A-1788 CH₃ Cl F CF₃ CH₃ A-1789 CF₃ Cl F CF₃ CH₃ A-1790 OCH₃ Cl F CF₃ CH₃ A-1791 F CH₃ F CF₃ CH₃ A-1792 Cl CH₃ F CF₃ CH₃ A-1793 CH₃ CH₃ F CF₃ CH₃ A-1794 CF₃ CH₃ F CF₃ CH₃ A-1795 OCH₃ CH₃ F CF₃ CH₃ A-1796 F CF₃ F CF₃ CH₃ A-1797 Cl CF₃ F CF₃ CH₃ A-1798 CH₃ CF₃ F CF₃ CH₃ A-1799 CF₃ CF₃ F CF₃ CH₃ A-1800 OCH₃ CF₃ F CF₃ CH₃ A-1801 F H Cl CF₃ CH₃ A-1802 Cl H Cl CF₃ CH₃ A-1803 CH₃ H Cl CF₃ CH₃ A-1804 CF₃ H Cl CF₃ CH₃ A-1805 OCH₃ H Cl CF₃ CH₃ A-1806 F F Cl CF₃ CH₃ A-1807 Cl F Cl CF₃ CH₃ A-1808 CH₃ F Cl CF₃ CH₃ A-1809 CF₃ F Cl CF₃ CH₃ A-1810 OCH₃ F Cl CF₃ CH₃ A-1811 F Cl Cl CF₃ CH₃ A-1812 Cl Cl Cl CF₃ CH₃ A-1813 CH₃ Cl Cl CF₃ CH₃ A-1814 CF₃ Cl Cl CF₃ CH₃ A-1815 OCH₃ Cl Cl CF₃ CH₃ A-1816 F CH₃ Cl CF₃ CH₃ A-1817 Cl CH₃ Cl CF₃ CH₃ A-1818 CH₃ CH₃ Cl CF₃ CH₃ A-1819 CF₃ CH₃ Cl CF₃ CH₃ A-1820 OCH₃ CH₃ Cl CF₃ CH₃ A-1821 F CF₃ Cl CF₃ CH₃ A-1822 Cl CF₃ Cl CF₃ CH₃ A-1823 CH₃ CF₃ Cl CF₃ CH₃ A-1824 CF₃ CF₃ Cl CF₃ CH₃ A-1825 OCH₃ CF₃ Cl CF₃ CH₃ A-1826 F H CH₃ CF₃ CH₃ A-1827 Cl H CH₃ CF₃ CH₃ A-1828 CH₃ H CH₃ CF₃ CH₃ A-1829 CF₃ H CH₃ CF₃ CH₃ A-1830 OCH₃ H CH₃ CF₃ CH₃ A-1831 F F CH₃ CF₃ CH₃ A-1832 Cl F CH₃ CF₃ CH₃ A-1833 CH₃ F CH₃ CF₃ CH₃ A-1834 CF₃ F CH₃ CF₃ CH₃ A-1835 OCH₃ F CH₃ CF₃ CH₃ A-1836 F Cl CH₃ CF₃ CH₃ A-1837 Cl Cl CH₃ CF₃ CH₃ A-1838 CH₃ Cl CH₃ CF₃ CH₃ A-1839 CF₃ Cl CH₃ CF₃ CH₃ A-1840 OCH₃ Cl CH₃ CF₃ CH₃ A-1841 F CH₃ CH₃ CF₃ CH₃ A-1842 Cl CH₃ CH₃ CF₃ CH₃ A-1843 CH₃ CH₃ CH₃ CF₃ CH₃ A-1844 CF₃ CH₃ CH₃ CF₃ CH₃ A-1845 OCH₃ CH₃ CH₃ CF₃ CH₃ A-1846 F CF₃ CH₃ CF₃ CH₃ A-1847 Cl CF₃ CH₃ CF₃ CH₃ A-1848 CH₃ CF₃ CH₃ CF₃ CH₃ A-1849 CF₃ CF₃ CH₃ CF₃ CH₃ A-1850 OCH₃ CF₃ CH₃ CF₃ CH₃ A-1851 F H CF₃ CF₃ CH₃ A-1852 Cl H CF₃ CF₃ CH₃ A-1853 CH₃ H CF₃ CF₃ CH₃ A-1854 CF₃ H CF₃ CF₃ CH₃ A-1855 OCH₃ H CF₃ CF₃ CH₃ A-1856 F F CF₃ CF₃ CH₃ A-1857 Cl F CF₃ CF₃ CH₃ A-1858 CH₃ F CF₃ CF₃ CH₃ A-1859 CF₃ F CF₃ CF₃ CH₃ A-1860 OCH₃ F CF₃ CF₃ CH₃ A-1861 F Cl CF₃ CF₃ CH₃ A-1862 Cl Cl CF₃ CF₃ CH₃ A-1863 CH₃ Cl CF₃ CF₃ CH₃ A-1864 CF₃ Cl CF₃ CF₃ CH₃ A-1865 OCH₃ Cl CF₃ CF₃ CH₃ A-1866 F CH₃ CF₃ CF₃ CH₃ A-1867 Cl CH₃ CF₃ CF₃ CH₃ A-1868 CH₃ CH₃ CF₃ CF₃ CH₃ A-1869 CF₃ CH₃ CF₃ CF₃ CH₃ A-1870 OCH₃ CH₃ CF₃ CF₃ CH₃ A-1871 F CF₃ CF₃ CF₃ CH₃ A-1872 Cl CF₃ CF₃ CF₃ CH₃ A-1873 CH₃ CF₃ CF₃ CF₃ CH₃ A-1874 CF₃ CF₃ CF₃ CF₃ CH₃ A-1875 OCH₃ CF₃ CF₃ CF₃ CH₃ A-1876 F H H H CF₃ A-1877 Cl H H H CF₃ A-1878 CH₃ H H H CF₃ A-1879 CF₃ H H H CF₃ A-1880 OCH₃ H H H CF₃ A-1881 F F H H CF₃ A-1882 Cl F H H CF₃ A-1883 CH₃ F H H CF₃ A-1884 CF₃ F H H CF₃ A-1885 OCH₃ F H H CF₃ A-1886 F Cl H H CF₃ A-1887 Cl Cl H H CF₃ A-1888 CH₃ Cl H H CF₃ A-1889 CF₃ Cl H H CF₃ A-1890 OCH₃ Cl H H CF₃ A-1891 F CH₃ H H CF₃ A-1892 Cl CH₃ H H CF₃ A-1893 CH₃ CH₃ H H CF₃ A-1894 CF₃ CH₃ H H CF₃ A-1895 OCH₃ CH₃ H H CF₃ A-1896 F CF₃ H H CF₃ A-1897 Cl CF₃ H H CF₃ A-1898 CH₃ CF₃ H H CF₃ A-1899 CF₃ CF₃ H H CF₃ A-1900 OCH₃ CF₃ H H CF₃ A-1901 F H F H CF₃ A-1902 Cl H F H CF₃ A-1903 CH₃ H F H CF₃ A-1904 CF₃ H F H CF₃ A-1905 OCH₃ H F H CF₃ A-1906 F F F H CF₃ A-1907 Cl F F H CF₃ A-1908 CH₃ F F H CF₃ A-1909 CF₃ F F H CF₃ A-1910 OCH₃ F F H CF₃ A-1911 F Cl F H CF₃ A-1912 Cl Cl F H CF₃ A-1913 CH₃ Cl F H CF₃ A-1914 CF₃ Cl F H CF₃ A-1915 OCH₃ Cl F H CF₃ A-1916 F CH₃ F H CF₃ A-1917 Cl CH₃ F H CF₃ A-1918 CH₃ CH₃ F H CF₃ A-1919 CF₃ CH₃ F H CF₃ A-1920 OCH₃ CH₃ F H CF₃ A-1921 F CF₃ F H CF₃ A-1922 Cl CF₃ F H CF₃ A-1923 CH₃ CF₃ F H CF₃ A-1924 CF₃ CF₃ F H CF₃ A-1925 OCH₃ CF₃ F H CF₃ A-1926 F H Cl H CF₃ A-1927 Cl H Cl H CF₃ A-1928 CH₃ H Cl H CF₃ A-1929 CF₃ H Cl H CF₃ A-1930 OCH₃ H Cl H CF₃ A-1931 F F Cl H CF₃ A-1932 Cl F Cl H CF₃ A-1933 CH₃ F Cl H CF₃ A-1934 CF₃ F Cl H CF₃ A-1935 OCH₃ F Cl H CF₃ A-1936 F Cl Cl H CF₃ A-1937 Cl Cl Cl H CF₃ A-1938 CH₃ Cl Cl H CF₃ A-1939 CF₃ Cl Cl H CF₃ A-1940 OCH₃ Cl Cl H CF₃ A-1941 F CH₃ Cl H CF₃ A-1942 Cl CH₃ Cl H CF₃ A-1943 CH₃ CH₃ Cl H CF₃ A-1944 CF₃ CH₃ Cl H CF₃ A-1945 OCH₃ CH₃ Cl H CF₃ A-1946 F CF₃ Cl H CF₃ A-1947 Cl CF₃ Cl H CF₃ A-1948 CH₃ CF₃ Cl H CF₃ A-1949 CF₃ CF₃ Cl H CF₃ A-1950 OCH₃ CF₃ Cl H CF₃ A-1951 F H CH₃ H CF₃ A-1952 Cl H CH₃ H CF₃ A-1953 CH₃ H CH₃ H CF₃ A-1954 CF₃ H CH₃ H CF₃ A-1955 OCH₃ H CH₃ H CF₃ A-1956 F F CH₃ H CF₃ A-1957 Cl F CH₃ H CF₃ A-1958 CH₃ F CH₃ H CF₃ A-1959 CF₃ F CH₃ H CF₃ A-1960 OCH₃ F CH₃ H CF₃ A-1961 F Cl CH₃ H CF₃ A-1962 Cl Cl CH₃ H CF₃ A-1963 CH₃ Cl CH₃ H CF₃ A-1964 CF₃ Cl CH₃ H CF₃ A-1965 OCH₃ Cl CH₃ H CF₃ A-1966 F CH₃ CH₃ H CF₃ A-1967 Cl CH₃ CH₃ H CF₃ A-1968 CH₃ CH₃ CH₃ H CF₃ A-1969 CF₃ CH₃ CH₃ H CF₃ A-1970 OCH₃ CH₃ CH₃ H CF₃ A-1971 F CF₃ CH₃ H CF₃ A-1972 Cl CF₃ CH₃ H CF₃ A-1973 CH₃ CF₃ CH₃ H CF₃ A-1974 CF₃ CF₃ CH₃ H CF₃ A-1975 OCH₃ CF₃ CH₃ H CF₃ A-1976 F H CF₃ H CF₃ A-1977 Cl H CF₃ H CF₃ A-1978 CH₃ H CF₃ H CF₃ A-1979 CF₃ H CF₃ H CF₃ A-1980 OCH₃ H CF₃ H CF₃ A-1981 F F CF₃ H CF₃ A-1982 Cl F CF₃ H CF₃ A-1983 CH₃ F CF₃ H CF₃ A-1984 CF₃ F CF₃ H CF₃ A-1985 OCH₃ F CF₃ H CF₃ A-1986 F Cl CF₃ H CF₃ A-1987 Cl Cl CF₃ H CF₃ A-1988 CH₃ Cl CF₃ H CF₃ A-1989 CF₃ Cl CF₃ H CF₃ A-1990 OCH₃ Cl CF₃ H CF₃ A-1991 F CH₃ CF₃ H CF₃ A-1992 Cl CH₃ CF₃ H CF₃ A-1993 CH₃ CH₃ CF₃ H CF₃ A-1994 CF₃ CH₃ CF₃ H CF₃ A-1995 OCH₃ CH₃ CF₃ H CF₃ A-1996 F CF₃ CF₃ H CF₃ A-1997 Cl CF₃ CF₃ H CF₃ A-1998 CH₃ CF₃ CF₃ H CF₃ A-1999 CF₃ CF₃ CF₃ H CF₃ A-2000 OCH₃ CF₃ CF₃ H CF₃ A-2001 F H H F CF₃ A-2002 Cl H H F CF₃ A-2003 CH₃ H H F CF₃ A-2004 CF₃ H H F CF₃ A-2005 OCH₃ H H F CF₃ A-2006 F F H F CF₃ A-2007 Cl F H F CF₃ A-2008 CH₃ F H F CF₃ A-2009 CF₃ F H F CF₃ A-2010 OCH₃ F H F CF₃ A-2011 F Cl H F CF₃ A-2012 Cl Cl H F CF₃ A-2013 CH₃ Cl H F CF₃ A-2014 CF₃ Cl H F CF₃ A-2015 OCH₃ Cl H F CF₃ A-2016 F CH₃ H F CF₃ A-2017 Cl CH₃ H F CF₃ A-2018 CH₃ CH₃ H F CF₃ A-2019 CF₃ CH₃ H F CF₃ A-2020 OCH₃ CH₃ H F CF₃ A-2021 F CF₃ H F CF₃ A-2022 Cl CF₃ H F CF₃ A-2023 CH₃ CF₃ H F CF₃ A-2024 CF₃ CF₃ H F CF₃ A-2025 OCH₃ CF₃ H F CF₃ A-2026 F H F F CF₃ A-2027 Cl H F F CF₃ A-2028 CH₃ H F F CF₃ A-2029 CF₃ H F F CF₃ A-2030 OCH₃ H F F CF₃ A-2031 F F F F CF₃ A-2032 Cl F F F CF₃ A-2033 CH₃ F F F CF₃ A-2034 CF₃ F F F CF₃ A-2035 OCH₃ F F F CF₃ A-2036 F Cl F F CF₃ A-2037 Cl Cl F F CF₃ A-2038 CH₃ Cl F F CF₃ A-2039 CF₃ Cl F F CF₃ A-2040 OCH₃ Cl F F CF₃ A-2041 F CH₃ F F CF₃ A-2042 Cl CH₃ F F CF₃ A-2043 CH₃ CH₃ F F CF₃ A-2044 CF₃ CH₃ F F CF₃ A-2045 OCH₃ CH₃ F F CF₃ A-2046 F CF₃ F F CF₃ A-2047 Cl CF₃ F F CF₃ A-2048 CH₃ CF₃ F F CF₃ A-2049 CF₃ CF₃ F F CF₃ A-2050 OCH₃ CF₃ F F CF₃ A-2051 F H Cl F CF₃ A-2052 Cl H Cl F CF₃ A-2053 CH₃ H Cl F CF₃ A-2054 CF₃ H Cl F CF₃ A-2055 OCH₃ H Cl F CF₃ A-2056 F F Cl F CF₃ A-2057 Cl F Cl F CF₃ A-2058 CH₃ F Cl F CF₃ A-2059 CF₃ F Cl F CF₃ A-2060 OCH₃ F Cl F CF₃ A-2061 F Cl Cl F CF₃ A-2062 Cl Cl Cl F CF₃ A-2063 CH₃ Cl Cl F CF₃ A-2064 CF₃ Cl Cl F CF₃ A-2065 OCH₃ Cl Cl F CF₃ A-2066 F CH₃ Cl F CF₃ A-2067 Cl CH₃ Cl F CF₃ A-2068 CH₃ CH₃ Cl F CF₃ A-2069 CF₃ CH₃ Cl F CF₃ A-2070 OCH₃ CH₃ Cl F CF₃ A-2071 F CF₃ Cl F CF₃ A-2072 Cl CF₃ Cl F CF₃ A-2073 CH₃ CF₃ Cl F CF₃ A-2074 CF₃ CF₃ Cl F CF₃ A-2075 OCH₃ CF₃ Cl F CF₃ A-2076 F H CH₃ F CF₃ A-2077 Cl H CH₃ F CF₃ A-2078 CH₃ H CH₃ F CF₃ A-2079 CF₃ H CH₃ F CF₃ A-2080 OCH₃ H CH₃ F CF₃ A-2081 F F CH₃ F CF₃ A-2082 Cl F CH₃ F CF₃ A-2083 CH₃ F CH₃ F CF₃ A-2084 CF₃ F CH₃ F CF₃ A-2085 OCH₃ F CH₃ F CF₃ A-2086 F Cl CH₃ F CF₃ A-2087 Cl Cl CH₃ F CF₃ A-2088 CH₃ Cl CH₃ F CF₃ A-2089 CF₃ Cl CH₃ F CF₃ A-2090 OCH₃ Cl CH₃ F CF₃ A-2091 F CH₃ CH₃ F CF₃ A-2092 Cl CH₃ CH₃ F CF₃ A-2093 CH₃ CH₃ CH₃ F CF₃ A-2094 CF₃ CH₃ CH₃ F CF₃ A-2095 OCH₃ CH₃ CH₃ F CF₃ A-2096 F CF₃ CH₃ F CF₃ A-2097 Cl CF₃ CH₃ F CF₃ A-2098 CH₃ CF₃ CH₃ F CF₃ A-2099 CF₃ CF₃ CH₃ F CF₃ A-2100 OCH₃ CF₃ CH₃ F CF₃ A-2101 F H CF₃ F CF₃ A-2102 Cl H CF₃ F CF₃ A-2103 CH₃ H CF₃ F CF₃ A-2104 CF₃ H CF₃ F CF₃ A-2105 OCH₃ H CF₃ F CF₃ A-2106 F F CF₃ F CF₃ A-2107 Cl F CF₃ F CF₃ A-2108 CH₃ F CF₃ F CF₃ A-2109 CF₃ F CF₃ F CF₃ A-2110 OCH₃ F CF₃ F CF₃ A-2111 F Cl CF₃ F CF₃ A-2112 Cl Cl CF₃ F CF₃ A-2113 CH₃ Cl CF₃ F CF₃ A-2114 CF₃ Cl CF₃ F CF₃ A-2115 OCH₃ Cl CF₃ F CF₃ A-2116 F CH₃ CF₃ F CF₃ A-2117 Cl CH₃ CF₃ F CF₃ A-2118 CH₃ CH₃ CF₃ F CF₃ A-2119 CF₃ CH₃ CF₃ F CF₃ A-2120 OCH₃ CH₃ CF₃ F CF₃ A-2121 F CF₃ CF₃ F CF₃ A-2122 Cl CF₃ CF₃ F CF₃ A-2123 CH₃ CF₃ CF₃ F CF₃ A-2124 CF₃ CF₃ CF₃ F CF₃ A-2125 OCH₃ CF₃ CF₃ F CF₃ A-2126 F H H Cl CF₃ A-2127 Cl H H Cl CF₃ A-2128 CH₃ H H Cl CF₃ A-2129 CF₃ H H Cl CF₃ A-2130 OCH₃ H H Cl CF₃ A-2131 F F H Cl CF₃ A-2132 Cl F H Cl CF₃ A-2133 CH₃ F H Cl CF₃ A-2134 CF₃ F H Cl CF₃ A-2135 OCH₃ F H Cl CF₃ A-2136 F Cl H Cl CF₃ A-2137 Cl Cl H Cl CF₃ A-2138 CH₃ Cl H Cl CF₃ A-2139 CF₃ Cl H Cl CF₃ A-2140 OCH₃ Cl H Cl CF₃ A-2141 F CH₃ H Cl CF₃ A-2142 Cl CH₃ H Cl CF₃ A-2143 CH₃ CH₃ H Cl CF₃ A-2144 CF₃ CH₃ H Cl CF₃ A-2145 OCH₃ CH₃ H Cl CF₃ A-2146 F CF₃ H Cl CF₃ A-2147 Cl CF₃ H Cl CF₃ A-2148 CH₃ CF₃ H Cl CF₃ A-2149 CF₃ CF₃ H Cl CF₃ A-2150 OCH₃ CF₃ H Cl CF₃ A-2151 F H F Cl CF₃ A-2152 Cl H F Cl CF₃ A-2153 CH₃ H F Cl CF₃ A-2154 CF₃ H F Cl CF₃ A-2155 OCH₃ H F Cl CF₃ A-2156 F F F Cl CF₃ A-2157 Cl F F Cl CF₃ A-2158 CH₃ F F Cl CF₃ A-2159 CF₃ F F Cl CF₃ A-2160 OCH₃ F F Cl CF₃ A-2161 F Cl F Cl CF₃ A-2162 Cl Cl F Cl CF₃ A-2163 CH₃ Cl F Cl CF₃ A-2164 CF₃ Cl F Cl CF₃ A-2165 OCH₃ Cl F Cl CF₃ A-2166 F CH₃ F Cl CF₃ A-2167 Cl CH₃ F Cl CF₃ A-2168 CH₃ CH₃ F Cl CF₃ A-2169 CF₃ CH₃ F Cl CF₃ A-2170 OCH₃ CH₃ F Cl CF₃ A-2171 F CF₃ F Cl CF₃ A-2172 Cl CF₃ F Cl CF₃ A-2173 CH₃ CF₃ F Cl CF₃ A-2174 CF₃ CF₃ F Cl CF₃ A-2175 OCH₃ CF₃ F Cl CF₃ A-2176 F H Cl Cl CF₃ A-2177 Cl H Cl Cl CF₃ A-2178 CH₃ H Cl Cl CF₃ A-2179 CF₃ H Cl Cl CF₃ A-2180 OCH₃ H Cl Cl CF₃ A-2181 F F Cl Cl CF₃ A-2182 Cl F Cl Cl CF₃ A-2183 CH₃ F Cl Cl CF₃ A-2184 CF₃ F Cl Cl CF₃ A-2185 OCH₃ F Cl Cl CF₃ A-2186 F Cl Cl Cl CF₃ A-2187 Cl Cl Cl Cl CF₃ A-2188 CH₃ Cl Cl Cl CF₃ A-2189 CF₃ Cl Cl Cl CF₃ A-2190 OCH₃ Cl Cl Cl CF₃ A-2191 F CH₃ Cl Cl CF₃ A-2192 Cl CH₃ Cl Cl CF₃ A-2193 CH₃ CH₃ Cl Cl CF₃ A-2194 CF₃ CH₃ Cl Cl CF₃ A-2195 OCH₃ CH₃ Cl Cl CF₃ A-2196 F CF₃ Cl Cl CF₃ A-2197 Cl CF₃ Cl Cl CF₃ A-2198 CH₃ CF₃ Cl Cl CF₃ A-2199 CF₃ CF₃ Cl Cl CF₃ A-2200 OCH₃ CF₃ Cl Cl CF₃ A-2201 F H CH₃ Cl CF₃ A-2202 Cl H CH₃ Cl CF₃ A-2203 CH₃ H CH₃ Cl CF₃ A-2204 CF₃ H CH₃ Cl CF₃ A-2205 OCH₃ H CH₃ Cl CF₃ A-2206 F F CH₃ Cl CF₃ A-2207 Cl F CH₃ Cl CF₃ A-2208 CH₃ F CH₃ Cl CF₃ A-2209 CF₃ F CH₃ Cl CF₃ A-2210 OCH₃ F CH₃ Cl CF₃ A-2211 F Cl CH₃ Cl CF₃ A-2212 Cl Cl CH₃ Cl CF₃ A-2213 CH₃ Cl CH₃ Cl CF₃ A-2214 CF₃ Cl CH₃ Cl CF₃ A-2215 OCH₃ Cl CH₃ Cl CF₃ A-2216 F CH₃ CH₃ Cl CF₃ A-2217 Cl CH₃ CH₃ Cl CF₃ A-2218 CH₃ CH₃ CH₃ Cl CF₃ A-2219 CF₃ CH₃ CH₃ Cl CF₃ A-2220 OCH₃ CH₃ CH₃ Cl CF₃ A-2221 F CF₃ CH₃ Cl CF₃ A-2222 Cl CF₃ CH₃ Cl CF₃ A-2223 CH₃ CF₃ CH₃ Cl CF₃ A-2224 CF₃ CF₃ CH₃ Cl CF₃ A-2225 OCH₃ CF₃ CH₃ Cl CF₃ A-2226 F H CF₃ Cl CF₃ A-2227 Cl H CF₃ Cl CF₃ A-2228 CH₃ H CF₃ Cl CF₃ A-2229 CF₃ H CF₃ Cl CF₃ A-2230 OCH₃ H CF₃ Cl CF₃ A-2231 F F CF₃ Cl CF₃ A-2232 Cl F CF₃ Cl CF₃ A-2233 CH₃ F CF₃ Cl CF₃ A-2234 CF₃ F CF₃ Cl CF₃ A-2235 OCH₃ F CF₃ Cl CF₃ A-2236 F Cl CF₃ Cl CF₃ A-2237 Cl Cl CF₃ Cl CF₃ A-2238 CH₃ Cl CF₃ Cl CF₃ A-2239 CF₃ Cl CF₃ Cl CF₃ A-2240 OCH₃ Cl CF₃ Cl CF₃ A-2241 F CH₃ CF₃ Cl CF₃ A-2242 Cl CH₃ CF₃ Cl CF₃ A-2243 CH₃ CH₃ CF₃ Cl CF₃ A-2244 CF₃ CH₃ CF₃ Cl CF₃ A-2245 OCH₃ CH₃ CF₃ Cl CF₃ A-2246 F CF₃ CF₃ Cl CF₃ A-2247 Cl CF₃ CF₃ Cl CF₃ A-2248 CH₃ CF₃ CF₃ Cl CF₃ A-2249 CF₃ CF₃ CF₃ Cl CF₃ A-2250 OCH₃ CF₃ CF₃ Cl CF₃ A-2251 F H H CH₃ CF₃ A-2252 Cl H H CH₃ CF₃ A-2253 CH₃ H H CH₃ CF₃ A-2254 CF₃ H H CH₃ CF₃ A-2255 OCH₃ H H CH₃ CF₃ A-2256 F F H CH₃ CF₃ A-2257 Cl F H CH₃ CF₃ A-2258 CH₃ F H CH₃ CF₃ A-2259 CF₃ F H CH₃ CF₃ A-2260 OCH₃ F H CH₃ CF₃ A-2261 F Cl H CH₃ CF₃ A-2262 Cl Cl H CH₃ CF₃ A-2263 CH₃ Cl H CH₃ CF₃ A-2264 CF₃ Cl H CH₃ CF₃ A-2265 OCH₃ Cl H CH₃ CF₃ A-2266 F CH₃ H CH₃ CF₃ A-2267 Cl CH₃ H CH₃ CF₃ A-2268 CH₃ CH₃ H CH₃ CF₃ A-2269 CF₃ CH₃ H CH₃ CF₃ A-2270 OCH₃ CH₃ H CH₃ CF₃ A-2271 F CF₃ H CH₃ CF₃ A-2272 Cl CF₃ H CH₃ CF₃ A-2273 CH₃ CF₃ H CH₃ CF₃ A-2274 CF₃ CF₃ H CH₃ CF₃ A-2275 OCH₃ CF₃ H CH₃ CF₃ A-2276 F H F CH₃ CF₃ A-2277 Cl H F CH₃ CF₃ A-2278 CH₃ H F CH₃ CF₃ A-2279 CF₃ H F CH₃ CF₃ A-2280 OCH₃ H F CH₃ CF₃ A-2281 F F F CH₃ CF₃ A-2282 Cl F F CH₃ CF₃ A-2283 CH₃ F F CH₃ CF₃ A-2284 CF₃ F F CH₃ CF₃ A-2285 OCH₃ F F CH₃ CF₃ A-2286 F Cl F CH₃ CF₃ A-2287 Cl Cl F CH₃ CF₃ A-2288 CH₃ Cl F CH₃ CF₃ A-2289 CF₃ Cl F CH₃ CF₃ A-2290 OCH₃ Cl F CH₃ CF₃ A-2291 F CH₃ F CH₃ CF₃ A-2292 Cl CH₃ F CH₃ CF₃ A-2293 CH₃ CH₃ F CH₃ CF₃ A-2294 CF₃ CH₃ F CH₃ CF₃ A-2295 OCH₃ CH₃ F CH₃ CF₃ A-2296 F CF₃ F CH₃ CF₃ A-2297 Cl CF₃ F CH₃ CF₃ A-2298 CH₃ CF₃ F CH₃ CF₃ A-2299 CF₃ CF₃ F CH₃ CF₃ A-2300 OCH₃ CF₃ F CH₃ CF₃ A-2301 F H Cl CH₃ CF₃ A-2302 Cl H Cl CH₃ CF₃ A-2303 CH₃ H Cl CH₃ CF₃ A-2304 CF₃ H Cl CH₃ CF₃ A-2305 OCH₃ H Cl CH₃ CF₃ A-2306 F F Cl CH₃ CF₃ A-2307 Cl F Cl CH₃ CF₃ A-2308 CH₃ F Cl CH₃ CF₃ A-2309 CF₃ F Cl CH₃ CF₃ A-2310 OCH₃ F Cl CH₃ CF₃ A-2311 F Cl Cl CH₃ CF₃ A-2312 Cl Cl Cl CH₃ CF₃ A-2313 CH₃ Cl Cl CH₃ CF₃ A-2314 CF₃ Cl Cl CH₃ CF₃ A-2315 OCH₃ Cl Cl CH₃ CF₃ A-2316 F CH₃ Cl CH₃ CF₃ A-2317 Cl CH₃ Cl CH₃ CF₃ A-2318 CH₃ CH₃ Cl CH₃ CF₃ A-2319 CF₃ CH₃ Cl CH₃ CF₃ A-2320 OCH₃ CH₃ Cl CH₃ CF₃ A-2321 F CF₃ Cl CH₃ CF₃ A-2322 Cl CF₃ Cl CH₃ CF₃ A-2323 CH₃ CF₃ Cl CH₃ CF₃ A-2324 CF₃ CF₃ Cl CH₃ CF₃ A-2325 OCH₃ CF₃ Cl CH₃ CF₃ A-2326 F H CH₃ CH₃ CF₃ A-2327 Cl H CH₃ CH₃ CF₃ A-2328 CH₃ H CH₃ CH₃ CF₃ A-2329 CF₃ H CH₃ CH₃ CF₃ A-2330 OCH₃ H CH₃ CH₃ CF₃ A-2331 F F CH₃ CH₃ CF₃ A-2332 Cl F CH₃ CH₃ CF₃ A-2333 CH₃ F CH₃ CH₃ CF₃ A-2334 CF₃ F CH₃ CH₃ CF₃ A-2335 OCH₃ F CH₃ CH₃ CF₃ A-2336 F Cl CH₃ CH₃ CF₃ A-2337 Cl Cl CH₃ CH₃ CF₃ A-2338 CH₃ Cl CH₃ CH₃ CF₃ A-2339 CF₃ Cl CH₃ CH₃ CF₃ A-2340 OCH₃ Cl CH₃ CH₃ CF₃ A-2341 F CH₃ CH₃ CH₃ CF₃ A-2342 Cl CH₃ CH₃ CH₃ CF₃ A-2343 CH₃ CH₃ CH₃ CH₃ CF₃ A-2344 CF₃ CH₃ CH₃ CH₃ CF₃ A-2345 OCH₃ CH₃ CH₃ CH₃ CF₃ A-2346 F CF₃ CH₃ CH₃ CF₃ A-2347 Cl CF₃ CH₃ CH₃ CF₃ A-2348 CH₃ CF₃ CH₃ CH₃ CF₃ A-2349 CF₃ CF₃ CH₃ CH₃ CF₃ A-2350 OCH₃ CF₃ CH₃ CH₃ CF₃ A-2351 F H CF₃ CH₃ CF₃ A-2352 Cl H CF₃ CH₃ CF₃ A-2353 CH₃ H CF₃ CH₃ CF₃ A-2354 CF₃ H CF₃ CH₃ CF₃ A-2355 OCH₃ H CF₃ CH₃ CF₃ A-2356 F F CF₃ CH₃ CF₃ A-2357 Cl F CF₃ CH₃ CF₃ A-2358 CH₃ F CF₃ CH₃ CF₃ A-2359 CF₃ F CF₃ CH₃ CF₃ A-2360 OCH₃ F CF₃ CH₃ CF₃ A-2361 F Cl CF₃ CH₃ CF₃ A-2362 Cl Cl CF₃ CH₃ CF₃ A-2363 CH₃ Cl CF₃ CH₃ CF₃ A-2364 CF₃ Cl CF₃ CH₃ CF₃ A-2365 OCH₃ Cl CF₃ CH₃ CF₃ A-2366 F CH₃ CF₃ CH₃ CF₃ A-2367 Cl CH₃ CF₃ CH₃ CF₃ A-2368 CH₃ CH₃ CF₃ CH₃ CF₃ A-2369 CF₃ CH₃ CF₃ CH₃ CF₃ A-2370 OCH₃ CH₃ CF₃ CH₃ CF₃ A-2371 F CF₃ CF₃ CH₃ CF₃ A-2372 Cl CF₃ CF₃ CH₃ CF₃ A-2373 CH₃ CF₃ CF₃ CH₃ CF₃ A-2374 CF₃ CF₃ CF₃ CH₃ CF₃ A-2375 OCH₃ CF₃ CF₃ CH₃ CF₃ A-2376 F H H CF₃ CF₃ A-2377 Cl H H CF₃ CF₃ A-2378 CH₃ H H CF₃ CF₃ A-2379 CF₃ H H CF₃ CF₃ A-2380 OCH₃ H H CF₃ CF₃ A-2381 F F H CF₃ CF₃ A-2382 Cl F H CF₃ CF₃ A-2383 CH₃ F H CF₃ CF₃ A-2384 CF₃ F H CF₃ CF₃ A-2385 OCH₃ F H CF₃ CF₃ A-2386 F Cl H CF₃ CF₃ A-2387 Cl Cl H CF₃ CF₃ A-2388 CH₃ Cl H CF₃ CF₃ A-2389 CF₃ Cl H CF₃ CF₃ A-2390 OCH₃ Cl H CF₃ CF₃ A-2391 F CH₃ H CF₃ CF₃ A-2392 Cl CH₃ H CF₃ CF₃ A-2393 CH₃ CH₃ H CF₃ CF₃ A-2394 CF₃ CH₃ H CF₃ CF₃ A-2395 OCH₃ CH₃ H CF₃ CF₃ A-2396 F CF₃ H CF₃ CF₃ A-2397 Cl CF₃ H CF₃ CF₃ A-2398 CH₃ CF₃ H CF₃ CF₃ A-2399 CF₃ CF₃ H CF₃ CF₃ A-2400 OCH₃ CF₃ H CF₃ CF₃ A-2401 F H F CF₃ CF₃ A-2402 Cl H F CF₃ CF₃ A-2403 CH₃ H F CF₃ CF₃ A-2404 CF₃ H F CF₃ CF₃ A-2405 OCH₃ H F CF₃ CF₃ A-2406 F F F CF₃ CF₃ A-2407 Cl F F CF₃ CF₃ A-2408 CH₃ F F CF₃ CF₃ A-2409 CF₃ F F CF₃ CF₃ A-2410 OCH₃ F F CF₃ CF₃ A-2411 F Cl F CF₃ CF₃ A-2412 Cl Cl F CF₃ CF₃ A-2413 CH₃ Cl F CF₃ CF₃ A-2414 CF₃ Cl F CF₃ CF₃ A-2415 OCH₃ Cl F CF₃ CF₃ A-2416 F CH₃ F CF₃ CF₃ A-2417 Cl CH₃ F CF₃ CF₃ A-2418 CH₃ CH₃ F CF₃ CF₃ A-2419 CF₃ CH₃ F CF₃ CF₃ A-2420 OCH₃ CH₃ F CF₃ CF₃ A-2421 F CF₃ F CF₃ CF₃ A-2422 Cl CF₃ F CF₃ CF₃ A-2423 CH₃ CF₃ F CF₃ CF₃ A-2424 CF₃ CF₃ F CF₃ CF₃ A-2425 OCH₃ CF₃ F CF₃ CF₃ A-2426 F H Cl CF₃ CF₃ A-2427 Cl H Cl CF₃ CF₃ A-2428 CH₃ H Cl CF₃ CF₃ A-2429 CF₃ H Cl CF₃ CF₃ A-2430 OCH₃ H Cl CF₃ CF₃ A-2431 F F Cl CF₃ CF₃ A-2432 Cl F Cl CF₃ CF₃ A-2433 CH₃ F Cl CF₃ CF₃ A-2434 CF₃ F Cl CF₃ CF₃ A-2435 OCH₃ F Cl CF₃ CF₃ A-2436 F Cl Cl CF₃ CF₃ A-2437 Cl Cl Cl CF₃ CF₃ A-2438 CH₃ Cl Cl CF₃ CF₃ A-2439 CF₃ Cl Cl CF₃ CF₃ A-2440 OCH₃ Cl Cl CF₃ CF₃ A-2441 F CH₃ Cl CF₃ CF₃ A-2442 Cl CH₃ Cl CF₃ CF₃ A-2443 CH₃ CH₃ Cl CF₃ CF₃ A-2444 CF₃ CH₃ Cl CF₃ CF₃ A-2445 OCH₃ CH₃ Cl CF₃ CF₃ A-2446 F CF₃ Cl CF₃ CF₃ A-2447 Cl CF₃ Cl CF₃ CF₃ A-2448 CH₃ CF₃ Cl CF₃ CF₃ A-2449 CF₃ CF₃ Cl CF₃ CF₃ A-2450 OCH₃ CF₃ Cl CF₃ CF₃ A-2451 F H CH₃ CF₃ CF₃ A-2452 Cl H CH₃ CF₃ CF₃ A-2453 CH₃ H CH₃ CF₃ CF₃ A-2454 CF₃ H CH₃ CF₃ CF₃ A-2455 OCH₃ H CH₃ CF₃ CF₃ A-2456 F F CH₃ CF₃ CF₃ A-2457 Cl F CH₃ CF₃ CF₃ A-2458 CH₃ F CH₃ CF₃ CF₃ A-2459 CF₃ F CH₃ CF₃ CF₃ A-2460 OCH₃ F CH₃ CF₃ CF₃ A-2461 F Cl CH₃ CF₃ CF₃ A-2462 Cl Cl CH₃ CF₃ CF₃ A-2463 CH₃ Cl CH₃ CF₃ CF₃ A-2464 CF₃ Cl CH₃ CF₃ CF₃ A-2465 OCH₃ Cl CH₃ CF₃ CF₃ A-2466 F CH₃ CH₃ CF₃ CF₃ A-2467 Cl CH₃ CH₃ CF₃ CF₃ A-2468 CH₃ CH₃ CH₃ CF₃ CF₃ A-2469 CF₃ CH₃ CH₃ CF₃ CF₃ A-2470 OCH₃ CH₃ CH₃ CF₃ CF₃ A-2471 F CF₃ CH₃ CF₃ CF₃ A-2472 Cl CF₃ CH₃ CF₃ CF₃ A-2473 CH₃ CF₃ CH₃ CF₃ CF₃ A-2474 CF₃ CF₃ CH₃ CF₃ CF₃ A-2475 OCH₃ CF₃ CH₃ CF₃ CF₃ A-2476 F H CF₃ CF₃ CF₃ A-2477 Cl H CF₃ CF₃ CF₃ A-2478 CH₃ H CF₃ CF₃ CF₃ A-2479 CF₃ H CF₃ CF₃ CF₃ A-2480 OCH₃ H CF₃ CF₃ CF₃ A-2481 F F CF₃ CF₃ CF₃ A-2482 Cl F CF₃ CF₃ CF₃ A-2483 CH₃ F CF₃ CF₃ CF₃ A-2484 CF₃ F CF₃ CF₃ CF₃ A-2485 OCH₃ F CF₃ CF₃ CF₃ A-2486 F Cl CF₃ CF₃ CF₃ A-2487 Cl Cl CF₃ CF₃ CF₃ A-2488 CH₃ Cl CF₃ CF₃ CF₃ A-2489 CF₃ Cl CF₃ CF₃ CF₃ A-2490 OCH₃ Cl CF₃ CF₃ CF₃ A-2491 F CH₃ CF₃ CF₃ CF₃ A-2492 Cl CH₃ CF₃ CF₃ CF₃ A-2493 CH₃ CH₃ CF₃ CF₃ CF₃ A-2494 CF₃ CH₃ CF₃ CF₃ CF₃ A-2495 OCH₃ CH₃ CF₃ CF₃ CF₃ A-2496 F CF₃ CF₃ CF₃ CF₃ A-2497 Cl CF₃ CF₃ CF₃ CF₃ A-2498 CH₃ CF₃ CF₃ CF₃ CF₃ A-2499 CF₃ CF₃ CF₃ CF₃ CF₃ A-2500 OCH₃ CF₃ CF₃ CF₃ CF₃

TABLE B Examples of preferred compounds of formula I′.1 are the compounds of formula I.1-B, (I′.1-B)

wherein R², R³, R⁴, R⁵ and R⁶ have the meanings corresponding to one line of the table 1 (compounds I′.1-B.1 to I′.1-B.2500).

TABLE C Examples of preferred compounds of formula I′.1 are the compounds of formula I′.1-C, (I′.1-C)

wherein R², R³, R⁴, R⁵ and R⁶ have the meanings corresponding to one line of the table 1 (compounds I′.1-C.1 to I′.1-C.2500).

TABLE D Examples of preferred compounds of formula I′.1 are the compounds of formula I′.1-D. (I′.1-D)

wherein R², R³, R⁴, R⁵ and R⁶ have the meanings corresponding to one line of the table 1 (compounds I′.1-D.1 to I′.1-D.2500).

TABLE E Examples of preferred compounds of formula I′.1 are the compounds of formula I′.1-E, (I′.1-E)

wherein R², R³, R⁴, R⁵ and R⁶ have the meanings corresponding to one line of the table 1 (compounds I′.1-E.1 to I′.1-E.2500).

TABLE F Examples of preferred compounds of formula I′.1 are the compounds of formula I′.1-F. (I′.1-F)

wherein R², R³, R⁴, R⁵ and R⁶ have the meanings corresponding to one line of the table 1 (compounds I′.1-F.1 to I′.1-F.2500).

TABLE G Examples of preferred compounds of formula I′.1 are the compounds of formula I′.1-G, (I′.1-G)

wherein R², R³, R⁴, R⁵ and R⁶ have the meanings corresponding to one line of the table 1 (compounds I′.1-G.1 to I′.1-G.2500).

TABLE H Examples of preferred compounds of formula I′.1 are the compounds of formula I′.1-H, (I′.1-H)

wherein R², R³, R⁴, R⁵ and R⁶ have the meanings corresponding to one line of the table 1 (compounds I′.1-H.1 to I′.1-H.2500).

TABLE J Examples of preferred compounds of formula I′.1 are the compounds of formula I′.1-J, (I′.1-J)

wherein R², R³, R⁴, R⁵ and R⁶ have the meanings corresponding to one line of the table 1 (compounds I′.1-J.1 to I′.1-J.2500).

TABLE K Examples of preferred compounds of formula I′.1 are the compounds of formula I′.1-K, (I′.1-K)

wherein R², R³, R⁴, R⁵ and R⁶ have the meanings corresponding to one line of the table 1 (compounds I′.1-K.1 to I′.1-K.2500).

TABLE L Examples of preferred compounds of formula I′.1 are the compounds of formula I′.1-L, (I′.1-L)

wherein R², R³, R⁴, R⁵ and R⁶ have the meanings corresponding to one line of the table 1 (compounds I′.1-L.1 to I′.1-L.2500).

TABLE M Examples of preferred compounds of formula I′.1 are the compounds of formula I′.1-M, (I′.1-M)

wherein R², R³, R⁴, R⁵ and R⁶ have the meanings corresponding to one line of the table 1 (compounds I′.1-M.1 to I′.1-M.2500).

TABLE N Examples of preferred compounds of formula I′.1 are the compounds of formula I′.1-N, (I′.1-N)

wherein R², R³, R⁴, R⁵ and R⁶ have the meanings corresponding to one line of the table 1 (compounds I′.1-N.1 to I′.1-N.2500).

TABLE O Examples of preferred compounds of formula I′.1 are the compounds of formula I′.1-O, (I′.1-O)

wherein R², R³, R⁴, R⁵ and R⁶ have the meanings corresponding to one line of the table 1 (compounds I′.1-O.1 to I′.1-O.2500).

TABLE P Examples of preferred compounds of formula I′.1 are the compounds of formula I′.1-P, (I′.1-P)

wherein R², R³, R⁴, R⁵ and R⁶ have the meanings corresponding to one line of the table 1 (compounds I′.1-P.1 to I′.1-P.2500).

TABLE Q Examples of preferred compounds of formula I′.1 are the compounds of formula I′.1-Q, (I′.1-Q)

wherein R², R³, R⁴, R⁵ and R⁶ have the meanings corresponding to one line of the table 1 (compounds I′.1-Q.1 to I′.1-Q.2500).

Preparation of the compounds of formula I can be accomplished according to the examples given in schemes 1 to 4 but are not limited to the routes given below:

The compounds of formula I.1 and I.2 can for instance be prepared according to the preparation procedures described in WO 2005/63724 as outlined in scheme 1 by reacting a compound of formula II.1 and/or its tautomer II.2 with a compound of formula III e.g. an alkylating agent, an acylating agent or the like. The major product of such a reaction is the compound of formula I.1, often being the only isomer isolated.

The compounds of formula II.1 and their tautomers of formula II.2. can for instance be prepared from the corresponding diphenylethylamines IV by the synthetic routes outlined in schemes 2 and 3. Compounds of the formula II.1 and their tautomers of formula II.2 with X being S can be obtained according to the method outlined in scheme 2.

According to the method outlined in scheme 2, a 1,2-diphenylaminoethane IV is converted into the corresponding isothiocyanate V by conventional means, e.g. by reacting IV with thiophosgene (see e.g. Houben-Weyl, E4, “Methoden der Organischen Chemie”, chapter IIIc, pp. 837-842). The isothiocyanate V is then reacted with an aminoethanol derivative of the formula VI, thereby obtaining the thiourea compound of the formula VII. The reaction of the aminoethanol derivative VI with isothiocyanate V can be performed in accordance with standard methods of organic chemistry, see e.g. Biosci. Biotech. Biochem. 1992, 56 (7), 1062-1065. The thus obtained thioureas can be cyclized by conventional means thereby obtaining the desired thiazoline compound of the formula II, with X being S. Cyclization of compound VII can be achieved e.g. under acid catalysis or under dehydrating conditions e.g. by Mitsunobu's reaction (see Tetrahedron Letters1999, 40, 3125-3128).

Compounds of the formula II, with X being O, can be obtained by the method outlined in scheme 3. In scheme 3 Y means OH or halogen and Z means hydrogen, alkyl or halogen, especially fluorine.

According to scheme 3, diphenylaminoethanes IV are converted into the corresponding carbamates of the formula VIII by reacting II with a phenyl chloroformate such as 4-chlorophenyl chloroformat according to standard methods (see e.g. Pesticide Biochemistry and Physiology 30, 1988, p. 190-197). The thus obtained carbamate VIII is reacted with the aminoethanol derivative of formula VI in the presence of trimethylchlorosilane according to the method described in J. Org. Chem. 1998, 63, 8515-8521. Thereby, 2-hydroxyethyl ureas of the formula VII.a {Y═OH} are obtained. The 2-hydroxyethylureas can be cyclized to the oxazoline compounds II according to the procedures described in Org. Lett. 1999, 1, 1705-1708 or Tetrahedron Lett. 1992, 33, 2807-2810.

Alternatively, substituted 2-chloroethyl ureas VII.a {Y=halogen} can be cyclized according to the methods described in Bioorg. Med. Chem. Lett. 1994, 4, 2317-2322.

In scheme 4 Hal is halogen, in particular chlorine. Chloroethyl ureas VII.a can be obtained from the corresponding diphenylethylamines of formula IV by reaction with 2-haloethylisocyanate IX, especially 2-chloroethylisocyanate.

The diphenylethylamines of formula IV can for instance be prepared by addition of appropriately substituted anion equivalents, for examples of organometallic compounds XII, to appropriately substituted C═N bond containing compounds XI (cf. for example Chem. Rev. 1998, 98, 1407-1438) as outlined in scheme 5.

Starting imines XI can for example be prepared by methods familiar to an organic chemist from the corresponding aldehydes X by reaction with amines in the presence of a dehydrating agent or from nitriles by reduction (e.g. J. Org. Chem. 1990, 55, 4199-4200) and are well known in the art. Starting imines XI include also chiral compounds as for example described in Tetrahedron 1999, 55, 8883-8904.

A general method for the preparation of compounds similar to the amines of formula IV starting from the corresponding carboxamides has been described in U.S. Pat. No. 4,536,599.

The compounds of formula I.2 can alternatively be obtained by converting primary amines of formula IV into secondary amines of formula XIV for instance by reductive amination (cf. scheme 6) followed by the addition of appropriately substituted isothiocyanates of formula XV, such as e. g. acetoxyethyl isothiocyanate, and subsequent saponification. The isothiocyanate of the formula XV can for instance be prepared according to the procedures described in Coll. Czech. Chem. Comm. 1986, 51, 112-117.

The thus obtained thioureas XVI can be cyclized by conventional means thereby obtaining the azoline compound of formula I.2. Cyclization of compound XVI can be achieved according to the reaction outlined in scheme 2 for the preparation of compounds of formula II.

Alternatively, the isothiocyanate V (cf. scheme 2) is reacted with an appropriately substituted aminoethanol of formula XVII, thereby obtaining the thiourea XVIII, as outlined in scheme 7. The reaction of the aminoethanol XVII with isothiocyanate V can be performed in accordance with the method outlined in scheme 2. The thiourea XVIII can be converted to the compound of formula I.1 according to the method outlined in schemes 2 or 7.

Alternatively, compounds of the general formula I.2 can be prepared according to scheme 8 and according to similar procedures described in WO 2006/125748 or for analogous benzylaminothiazolines in WO 2007/020377 by reacting appropriately substituted azolines XIV (cf. scheme 6) with azoline-compounds XIX.

As a rule, the compounds of the formula I can be prepared by the methods described above. If individual compounds cannot be prepared via the above-described routes, they can be prepared by derivatization of other compounds of formula I or by customary modifications of the synthesis routes described. For example, in individual cases, certain compounds of formula I can advantageously be prepared from other compounds of formula I by ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, oxidation and the like.

The reaction mixtures are worked up in the customary manner, for example by mixing with water, separating the phases, and, if appropriate, purifying the crude products by chromatography, for example on alumina or on silica gel. Some of the intermediates and end products may be obtained in the form of colourless or pale brown viscous oils which are freed or purified from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, they may be purified by recrystallization or digestion.

Due to their excellent activity, the compounds of formula I may be used for controlling animal pests.

Accordingly, the present invention also provides a method for controlling animal pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or a plant, plant propagation materials, soil, area, material or environment in which the pests are growing or may grow, or the materials, plants, plant propagation materials, soils, surfaces or spaces to be protected from pest attack or infestation with a pesticidally effective amount of a compound of the formula I or a salt thereof or a composition as defined above.

Preferably, the method of the invention serves for protecting plant propagation materials, in particular seeds, and the plant which grows therefrom from animal pest attack or infestation and comprises treating the plant propagation materials, in particular the seed, with a pesticidally effective amount of a compound of the formula I or an agriculturally acceptable salt thereof as defined above or with a pesticidally effective amount of an agricultural composition as defined above and below. The method of the invention is not limited to the protection of the “substrate” (plant, plant propagation materials such as seed, soil material etc.) which has been treated according to the invention, but also has a preventive effect, thus, for ex-ample, according protection to a plant which grows from a treated plant propagation materials, the plant itself not having been treated.

In the sense of the present invention, “animal pests” are preferably selected from arthropods and nematodes, more preferably from harmful insects, arachnids and nematodes, and even more preferably from insects, acarids and nematodes.

The invention further provides an agricultural composition for combating such animal pests, which comprises such an amount of at least one compound of the general formula I or at least one agriculturally useful salt thereof and at least one inert liquid and/or solid agronomically acceptable carrier that has a pesticidal action and, if desired, at least one surfactant.

Such a composition may contain a single active compound of the formula I or a salt thereof or a mixture of several active compounds of the formula I or their salts according to the pre-sent invention. The composition according to the present invention may comprise an individual isomer or mixtures of isomers as well as individual tautomers or mixtures of tautomers.

The compounds of the formula I and the pestidicidal compositions comprising them are effective agents for controlling arthropod pests and nematodes. Animal pests controlled by the compounds of formula I include for example:

insects from the order of the lepidopterans (Lepidoptera), for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis;

beetles (Coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria;

dipterans (Diptera), for example Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea and Tipula paludosa;

thrips (Thysanoptera), e.g. Dichromothrips corbetti, Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci;

hymenopterans (Hymenoptera), e.g. Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta;

heteropterans (Heteroptera), e.g. Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor;

homopterans (Homoptera), e.g. Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis forbesi, Aphis pomi, Aphis gossypii, Aphis grossulariae, Aphis schneideri, Aphis spiraecola, Aphis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Bemisia argentifolii, Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Dysaphis plantaginea, Dysaphis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzodes persicae, Myzus ascalonicus, Myzus cerasi, Myzus persicae, Myzus varians, Nasonovia ribisnigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Sogatella furcifera Trialeurodes vaporariorum, Toxoptera aurantiiand, and Viteus vitifolii;

termites (Isoptera), e.g. Calotermes flavicollis, Leucotermes flavipes, Reticulitermes flavipes, Reticulitermes lucifugus and Termes natalensis;

orthopterans (Orthoptera), e.g. Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus and Tachycines asynamorus;

Arachnoidea, such as arachnids (Acarina), e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp. such as Aculus schlechtendali, Phyllocoptrata oleivora and Eriophyes sheldoni; Tarsonemidae spp. such as Phytonemus pallidus and Polyphagotarsonemus latus; Tenuipalpidae spp. such as Brevipalpus phoenicis; Tetranychidae spp. such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and oligonychus pratensis;

Siphonatera, e.g. Xenopsylla cheopsis, Ceratophyllus spp.;

The compositions and compounds of formula I are useful for the control of nematodes, especially plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, and other Meloidogyne species;

cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species; Sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; Pine nematodes, Bursaphelenchus xylophilus and other Bursaphelenchus species; Ring nematodes, Criconema species, Criconemella species, Criconemoides species, Mesocriconema species; Stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species; Awl nematodes, Dolichodorus species; Spiral nematodes, Heliocotylenchus multicinctus and other Helicotylenchus species; Sheath and sheathoid nematodes, Hemicycliophora species and Hemicriconemoides species; Hirshmanniella species; Lance nematodes, Hoploaimus species; false rootknot nematodes, Nacobbus species; Needle nematodes, Longidorus elongatus and other Longidorus species; Pin nematodes, Paratylenchus species; Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; Burrowing nematodes, Radopholus similis and other Radopholus species; Reniform nematodes, Rotylenchus robustus and other Rotylenchus species; Scutellonema species; Stubby root nematodes, Trichodorus primitivus and other Trichodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species; Citrus nematodes, Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant parasitic nematode species.

In a preferred embodiment of the invention the compounds of formula I are used for controlling insects or arachnids, in particular insects of the orders Lepidoptera, Coleoptera, Thysanoptera and Homoptera and arachnids of the order Acarina. The compounds of the formula I according to the present invention are particularly useful for controlling insects of the order Thysanoptera and Homoptera.

The compounds of formula I or the pesticidal compositions comprising them may be used to protect growing plants and crops from attack or infestation by animal pests, especially insects, acaridae or arachnids by contacting the plant/crop with a pesticidally effective amount of compounds of formula I. The term “crop” refers both to growing and harvested crops.

The compounds of formula I can be converted into the customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules. The use form depends on the particular intended purpose; in each case, it should ensure a fine and even distribution of the compound according to the invention.

The formulations are prepared in a known manner (see e.g. for review U.S. Pat. No. 3,060,084, EP-A 707 445 (for liquid concentrates), Browning, “Agglomeration”, Chemical Engineering, Dec. 4, 1967, 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and et seq. WO 91/13546, U.S. Pat. No. 4,172,714, U.S. Pat. Nos. 4,144,050, 3,920,442, 5,180,587, 5,232,701, 5,208,030, GB 2,095,558, U.S. Pat. No. 3,299,566, Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989 and Mollet, H., Grubemann, A., Formulation technology, Wiley VCH Verlag GmbH, Weinheim (Germany), 2001, 2. D. A. Knowles, Chemistry and Technology of Agrochemical Formulations, Kluwer Academic Publishers, Dordrecht, 1998 (ISBN 0-7514-0443-8), for example by extending the active compound with auxiliaries suitable for the formulation of agrochemicals, such as solvents and/or carriers, if desired emulsifiers, surfactants and dispersants, preservatives, anti-foaming agents, anti-freezing agents, for seed treatment formulation also optionally colorants and/or binders and/or gelling agents.

Examples of suitable solvents are water, aromatic solvents (for example Solvesso products, xylene), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (N-methyl-pyrrolidone [NMP], N-octyl-pyrrolidone [NOP]), acetates (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids and fatty acid esters. In principle, solvent mixtures may also be used.

Suitable emulsifiers are non-ionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates).

Examples of dispersants are lignin-sulfite waste liquors and methylcellulose.

Suitable surfactants used are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sul-fonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty alcohol ethylene oxide conden-sates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignosulfite waste liquors and methylcellulose.

Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, highly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone or water.

Also anti-freezing agents such as glycerin, ethylene glycol, propylene glycol and bactericides such as can be added to the formulation.

Suitable antifoaming agents are for example antifoaming agents based on silicon or magnesium stearate.

A suitable preservative is e.g. dichlorophen.

Seed treatment formulations may additionally comprise binders and optionally colorants.

Binders can be added to improve the adhesion of the active materials on the seeds after treatment. Suitable binders are block copolymers EO/PO surfactants but also polyvinylalcoholsl, polyvinylpyrrolidones, polyacrylates, polymethacrylates, polybutenes, polyisobutylenes, polystyrene, polyethyleneamines, polyethyleneamides, polyethyleneimines (Lupasol®, Polymin®), polyethers, polyurethans, polyvinylacetate, tylose and copolymers derived from these polymers.

Optionally, also colorants can be included in the formulation. Suitable colorants or dyes for seed treatment formulations are Rhodamin B, C.I. Pigment Red 112, C.I. Solvent Red 1, pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 112, pigment red 48:2, pigment red 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.

Examples of a gelling agent is carrageen (Satiagel®).

Powders, materials for spreading and dustable products can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.

Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers.

Examples of solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.

In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active compound(s). In this case, the active compound(s) are employed in a purity of from 90% to 100% by weight, preferably 95% to 100% by weight (according to NMR spectrum).

For seed treatment purposes, respective formulations can be diluted 2-10 fold leading to concentrations in the ready to use preparations of 0.01 to 60% by weight active compound by weight, preferably 0.1 to 40% by weight.

The compounds of formula I can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend entirely on the intended pur-poses; they are intended to ensure in each case the finest possible distribution of the active compound(s) according to the invention.

Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier. However, it is also possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.

The active compound concentrations in the ready-to-use preparations can be varied within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1% per weight.

The active compound(s) may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active compound, or even to apply the active compound without additives.

The following are examples of formulations:

1. Products for dilution with water for foliar applications. For seed treatment purposes, such products may be applied to the seed diluted or undiluted.

A) Water-Soluble Concentrates (SL, LS)

10 parts by weight of the active compound(s) are dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetters or other auxiliaries are added. The active compound(s) dissolves upon dilution with water, whereby a formulation with 10% (w/w) of active compound(s) is obtained.

B) Dispersible Concentrates (DC)

20 parts by weight of the active compound(s) are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion, whereby a formulation with 20% (w/w) of active compound(s) is obtained.

C) Emulsifiable Concentrates (EC)

15 parts by weight of the active compound(s) are dissolved in 7 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion, whereby a formulation with 15% (w/w) of active compound(s) is obtained.

D) Emulsions (EW, EO, ES)

25 parts by weight of the active compound(s) are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is introduced into 30 parts by weight of water by means of an emulsifier machine (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion, whereby a formulation with 25% (w/w) of active compound(s) is obtained.

E) Suspensions (SC, OD, FS)

In an agitated ball mill, 20 parts by weight of the active compound(s) are comminuted with addition of 10 parts by weight of dispersants, wetters and 70 parts by weight of water or of an organic solvent to give a fine active compound(s) suspension. Dilution with water gives a stable suspension of the active compound(s), whereby a formulation with 20% (w/w) of active compound(s) is obtained.

F) Water-Dispersible Granules and Water-Soluble Granules (WG, SG)

50 parts by weight of the active compound(s) are ground finely with addition of 50 parts by weight of dispersants and wetters and made as water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound(s), whereby a formulation with 50% (w/w) of active compound(s) is obtained.

G) Water-Dispersible Powders and Water-Soluble Powders (WP, SP, SS, WS)

75 parts by weight of the active compound(s) are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound(s), whereby a formulation with 75% (w/w) of active compound(s) is obtained.

H) Gel-Formulation (GF)

In an agitated ball mill, 20 parts by weight of the active compound(s) are comminuted with addition of 10 parts by weight of dispersants, 1 part by weight of a gelling agent wetters and 70 parts by weight of water or of an organic solvent to give a fine active compound(s) suspension. Dilution with water gives a stable suspension of the active compound(s), whereby a formulation with 20% (w/w) of active compound(s) is obtained.

2. Products to be applied undiluted for foliar applications. For seed treatment purposes, such products may be applied to the seed diluted or undiluted.

I) Dustable Powders (DP, DS)

5 parts by weight of the active compound(s) are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dustable product having 5% (w/w) of active compound(s)

J) Granules (GR, FG, GG, MG)

0.5 parts by weight of the active compound(s) is ground finely and associated with 95.5 parts by weight of carriers, whereby a formulation with 0.5% (w/w) of active compound(s) is obtained. Current methods are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted for foliar use.

K) ULV Solutions (UL)

10 parts by weight of the active compound(s) are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product having 10% (w/w) of active compound(s), which is applied undiluted for foliar use.

The compounds of formula I are also suitable for the treatment of plant propagation materials such as seeds. Conventional seed treatment formulations include for example flowable concentrates FS, solutions LS, powders for dry treatment DS, water dispersible powders for slurry treatment WS, water soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having preger-minated the latter

In a preferred embodiment a FS formulation is used for seed treatment. Typically, a FS formulation may comprise 1-800 g/l of active ingredient, 1-200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.

Other preferred FS formulations of compounds of formula I for seed treatment comprise from 0.5 to 80 wt % of the active ingredient, from 0.05 to 5 wt % of a wetter, from 0.5 to 15 wt % of a dispersing agent, from 0.1 to 5 wt % of a thickener, from 5 to 20 wt % of an anti-freeze agent, from 0.1 to 2 wt % of an anti-foam agent, from 1 to 20 wt % of a pigment and/or a dye, from 0 to 15 wt % of a sticker/adhesion agent, from 0 to 75 wt % of a filler/vehicle, and from 0.01 to 1 wt % of a preservative.

Various types of oils, wetters, adjuvants, herbicides, fungicides, other pesticides, or bactericides may be added to the active ingredients, if appropriate just immediately prior to use (tank mix). These agents usually are admixed with the agents according to the invention in a weight ratio of 1:10 to 10:1.

The compounds of formula I are effective through both contact (via soil, glass, wall, bed net, carpet, plant parts or animal parts), and ingestion (bait, or plant part).

For use against ants, termites, wasps, flies, mosquitos, crickets, or cockroaches, compounds of formula I are preferably used in a bait composition.

The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). Solid baits can be formed into various shapes and forms suitable to the respective application e.g. granules, blocks, sticks, disks. Liquid baits can be filled into various devices to ensure proper application, e.g. open containers, spray devices, droplet sources, or evaporation sources. Gels can be based on aqueous or oily matrices and can be formulated to particular necessities in terms of stickiness, moisture retention or aging characteristics.

The bait employed in the composition is a product, which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitos, crickets etc. or cockroaches to eat it. The attractiveness can be manipulated by using feeding stimulants or sex pheromones. Food stimulants are chosen, for example, but not exclusively, from animal and/or plant proteins (meat-, fish- or blood meal, insect parts, egg yolk), from fats and oils of animal and/or plant origin, or mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant. Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature and are known to those skilled in the art.

Formulations of compounds of formula I as aerosols (e.g in spray cans), oil sprays or pump sprays are highly suitable for the non-professional user for controlling pests such as flies, fleas, ticks, mosquitos or cockroaches. Aerosol recipes are preferably composed of the active compound, solvents such as lower alcohols (e.g. methanol, ethanol, propanol, butanol), ketones (e.g. acetone, methyl ethyl ketone), paraffin hydrocarbons (e.g. kerosenes) having boiling ranges of approximately 50 to 250° C., dimethyl-formamide, N methylpyrrolidone, dimethyl sulphoxide, aromatic hydrocarbons such as toluene, xylene, water, furthermore auxiliaries such as emulsifiers such as sorbitol monooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fatty alcohol ethoxylate, perfume oils such as ethereal oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzoate, amphoteric surfactants, lower epoxides, triethyl orthoformate and, if required, propellants such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases.

The oil spray formulations differ from the aerosol recipes in that no propellants are used.

The compounds of formula I and their respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems.

Methods to control infectious diseases transmitted by insects (e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis) with compounds of formula I and their respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or the like. Insecticidal compositions for application to fibers, fabric, knitgoods, nonwovens, netting material or foils and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder. Suitable repellents for exam-ple are N,N-diethylmetatoluamide (DEET), N,N-diethylphenylacetamide (DEPA), 1-(3-cyclohexan-1-yl-carbonyl)-2-methylpiperine, (2-hydroxymethylcyclohexyl) acetic acid lactone, 2-ethyl-1,3-hexandiol, indalone, Methylneodecanamide (MNDA), a pyrethroid not used for insect control such as {(+/−)-3-allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)-trans-chrysantemate (Esbiothrin), a repellent derived from or identical with plant ex-tracts like limonene, eugenol, (+)-Eucamalol (1), (−)-1-epi-eucamalol or crude plant ex-tracts from plants like Eucalyptus maculata, Vitex rotundifolia, Cymbopogan martinii, Cymbopogan citratus (lemon grass), Cymopogan nartdus (citronella). Suitable binders are selected for example from polymers and copolymers of vinyl esters of aliphatic ac-ids (such as such as vinyl acetate and vinyl versatate), acrylic and methacrylic esters of alcohols, such as butyl acrylate, 2-ethylhexylacrylate, and methyl acrylate, mono- and diethylenically unsaturated hydrocarbons, such as styrene, and aliphatic diens, such as butadiene.

The impregnation of curtains and bednets is done in general by dipping the textile material into emulsions or dispersions of the compound of the formula I or spraying them onto the nets.

Methods which can be employed for treating the seed are, in principle, all suitable seed treatment and especially seed dressing techniques known in the art, such as seed coating (e.g. seed pelleting), seed dusting and seed imbibition (e.g. seed soaking). Here, “seed treatment” refers to all methods that bring seeds and the compounds of formula I into contact with each other, and “seed dressing” to methods of seed treatment which provide the seeds with an amount of the compounds of formula I, i.e. which generate a seed comprising the compound of formula I. In principle, the treatment can be applied to the seed at any time from the harvest of the seed to the sowing of the seed. The seed can be treated immediately before, or during, the planting of the seed, for example using the “planter's box” method. However, the treatment may also be carried out several weeks or months, for example up to 12 months, before planting the seed, for example in the form of a seed dressing treatment, without a substantially reduced efficacy being observed.

Expediently, the treatment is applied to unsown seed. As used herein, the term “unsown seed” is meant to include seed at any period from the harvest of the seed to the sowing of the seed in the ground for the purpose of germination and growth of the plant.

Specifically, a procedure is followed in the treatment in which the seed is mixed, in a suitable device, for example a mixing device for solid or solid/liquid mixing partners, with the desired amount of seed treatment formulations, either as such or after previous dilution with water, until the composition is distributed uniformly on the seed. If appropriate, this is followed by a drying step.

The compounds of formula I or the enantiomers or veterinarily acceptable salts thereof are in particular also suitable for being used for combating parasites in and on animals.

A further object of the present invention is thus to provide new methods for controlling parasites in and on animals. Another object of the invention is to provide safer pesticides for animals. Another object of the invention is further to provide pesticides for animals that may be used in lower doses than existing pesticides. And another object of the invention is to provide pesticides for animals, which provide a long residual control of the parasites.

The invention also relates to compositions containing a parasiticidally effective amount of compounds of formula I or the enantiomers, diastereomers or veterinarily acceptable salts thereof and an acceptable carrier, for combating parasites in and on animals.

The present invention also provides a method for treating, controlling, preventing and protecting animals against infestation and infection by parasites, which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of a compound of formula I or the enantiomers, diastereomers or veterinarily acceptable salts thereof or a composition comprising it.

The invention also provides a process for the preparation of a composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises a parasiticidally effective amount of a compound of formula I or the enantiomers, diastereomers or veterinarily acceptable salts thereof or a composition comprising it.

Activity of compounds against agricultural pests does not suggest their suitability for control of endo- and ectoparasites in and on animals which requires, for example, low, non-emetic dosages in the case of oral application, metabolic compatibility with the animal, low toxicity, and a safe handling.

Surprisingly, it has now been found that compounds of formula I are suitable for combating endo- and ectoparasites in and on animals.

Compounds of formula I or the enantiomers, diastereomers or veterinarily acceptable salts thereof and compositions comprising them are preferably used for controlling and preventing infestations and infections animals including warm-blooded animals (including humans) and fish. They are for example suitable for controlling and preventing infestations and infections in mammals such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in fur-bearing animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks and fish such as fresh- and salt-water fish such as trout, carp and eels.

Compounds of formula I or the enantiomers, diastereomers or veterinarily acceptable salts thereof and compositions comprising them are preferably used for controlling and preventing infestations and infections in domestic animals, such as dogs or cats.

Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas.

The compounds of formula I or the enantiomers, diastereomers or veterinarily acceptable salts thereof and compositions comprising them are suitable for systemic and/or non-systemic control of ecto- and/or endoparasites. They are active against all or some stages of development.

The compounds of formula I, the enantiomers, diastereomers or veterinarily acceptable salts thereof are especially useful for combating ectoparasites.

The compounds of formula I, the enantiomers, diastereomers or veterinarily acceptable salts thereof are especially useful for combating parasites of the following orders and species, respectively:

fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus,

cockroaches (Blattaria—Blattodea), e.g. Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis,

flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inor-nata, Culiseta melanura, Dermatobia hominis, Fannia canicularis, Gasterophilus intes-tinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Leptoconops torrens, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor, Prosimulium mixtum, Sarcophaga haemorrhoidalis, Sarcophaga sp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis,

lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus.

ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyomma americanum, Ambryomma maculatum, Ornithodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacoti and Dermanyssus gallinae,

Actinedida (Prostigmata) and Acaridida (Astigmata) e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., and Laminosioptes spp,

bugs (Heteropterida): Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp. and Arilus critatus,

Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp,

Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp,

Roundworms Nematoda:

Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae (Trichinella spp.), (Trichuridae) Trichuris spp., Capillaria spp,

Rhabditida, e.g. Rhabditis spp, Strongyloides spp., Helicephalobus spp,

Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus, Bunostomum spp. (Hookworm), Trichostrongylus spp., Haemonchus contortus., Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus, Syngamus trachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp. Aleurostrongylus abstrusus, and Dioctophyma renale,

Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascaris suum, Ascaridia galli, Parascaris equorum, Enterobius vermicularis (Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp., and Oxyuris equi,

Camallanida, e.g. Dracunculus medinensis (guinea worm)

Spirurida, e.g. Thelazia spp. Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp.a, Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronema spp.,

Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp., Macracanthorhynchus hirudinaceus and Oncicola spp,

Planarians (Plathelminthes):

Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilhar-zia spp., Alaria alata, Paragonimus spp., and Nanocyetes spp,

Cercomeromorpha, in particular Cestoda (Tapeworms), e.g. Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidium caninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp., and Hymenolepis spp.

The compounds of formula I and compositions containing them are particularly useful for the control of pests from the orders Diptera, Siphonaptera and Ixodida.

Moreover, the use of the formula I and compositions containing them for combating mosquitoes is especially preferred.

The use of the compounds of formula I, the enantiomers, diastereomers or veterinarily acceptable salts thereof and compositions containing them for combat-ing flies is a further preferred embodiment of the present invention.

Furthermore, the use of the compounds of formula I, the enantiomers, diastereomers or veterinarily acceptable salts thereof and compositions containing them for combating fleas is especially preferred.

The use of the compounds of formula formula I, the enantiomers, diastereomers or veterinarily acceptable salts thereof and compositions containing them for combating ticks is a further preferred embodiment of the present invention.

The compounds of the compounds of formula I, the enantiomers, diastereomers or veterinarily acceptable salts thereof also are especially useful for combating endoparasites (roundworms nematoda, thorny headed worms and planarians).

Administration can be carried out both prophylactically and therapeutically.

Administration of the active compounds is carried out directly or in the form of suitable preparations, orally, topically/dermally or parenterally.

For oral administration to warm-blooded animals, the compounds of formula I, the enantiomers, diastereomers or veterinarily acceptable salts thereof may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. In addi-tion, the formula I compounds may be administered to the animals in their drinking water. For oral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound (and likewise the enantiomers, diastereomers or veterinarily acceptable salts thereof), preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day.

Alternatively, the compounds of formula I, the enantiomers, diastereomers or veterinarily acceptable salts thereof may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection. The compounds of formula I, the enantiomers, diastereomers or veterinarily acceptable salts thereof may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the compounds of formula I, the enantiomers, diastereomers or veterinarily acceptable salts thereof may be formulated into an implant for subcutaneous administration. In addition the compound of formula I, the enantiomers, diastereomers or veterinarily acceptable salts thereof may be transdermally administered to animals. For parenteral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the compound of formula I (or the enantiomers, diastereomers or veterinarily acceptable salts thereof).

The compounds of formula I (and likewise the enantiomers, diastereomers or veterinarily acceptable salts thereof) may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the compound of formula I. In addition, the compounds of formula I, the enantiomers, diastereomers or veterinarily acceptable salts thereof may be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.

Suitable preparations are:

Solutions such as oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pouring-on formulations, gels;

Emulsions and suspensions for oral or dermal administration; semi-solid preparations;

Formulations in which the active compound is processed in an ointment base or in an oil-in-water or water-in-oil emulsion base;

Solid preparations such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalants, and active compound-containing shaped articles.

Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding further ingredients such as acids, bases, buffer salts, preservatives, and solubilizers. The solutions are filtered and filled sterile.

Suitable solvents are physiologically tolerable solvents such as water, alkanols such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycols, N-methylpyrrolidone, 2-pyrrolidone, and mixtures thereof.

The active compounds can optionally be dissolved in physiologically tolerable vegetable or synthetic oils which are suitable for injection.

Suitable solubilizers are solvents which promote the dissolution of the active compound in the main solvent or prevent its precipitation. Examples are polyvinylpyrrolidone, polyvinyl alcohol, polyoxyethylated castor oil, and polyoxyethylated sorbitan ester.

Suitable preservatives are benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid esters, and n-butanol.

Oral solutions are administered directly. Concentrates are administered orally after prior dilution to the use concentration. Oral solutions and concentrates are prepared according to the state of the art and as described above for injection solutions, sterile procedures not being necessary.

Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on.

Solutions for use on the skin are prepared according to the state of the art and according to what is described above for injection solutions, sterile procedures not being necessary.

Further suitable solvents are polypropylene glycol, phenyl ethanol, phenoxy ethanol, ester such as ethyl or butyl acetate, benzyl benzoate, ethers such as alkyleneglycol alkylether, e.g. dipropylenglycol monomethylether, ketons such as acetone, methylethylketone, aromatic hydrocarbons, vegetable and synthetic oils, dimethylformamide, dimethylacetamide, transcutol, solketal, propylencarbonate, and mixtures thereof.

It may be advantageous to add thickeners during preparation. Suitable thickeners are inorganic thickeners such as bentonites, colloidal silicic acid, aluminium monostearate, organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and methacrylates.

Gels are applied to or spread on the skin or introduced into body cavities. Gels are prepared by treating solutions which have been prepared as described in the case of the injection solutions with sufficient thickener that a clear material having an ointment-like consistency results. The thickeners employed are the thickeners given above.

Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically.

Pour-on formulations are prepared by dissolving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures. If appropriate, other auxiliaries such as colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives are added.

Suitable solvents are water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as alkylene glycol alkyl ethers such as dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether, ketones such as acetone, methyl ethyl ketone, cyclic carbonates such as propylene carbonate, ethylene carbonate, aromatic and/or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethylacetamide, n-alkylpyrrolidones such as methylpyrrolidone, n-butylpyrrolidone or n-octylpyrrolidone, N methylpyrrolidone, 2-pyrrolidone, 2,2-dimethyl-4-oxy-methylene-1,3-diox-olane and glycerol formal.

Suitable colorants are all colorants permitted for use on animals and which can be dissolved or suspended.

Suitable absorption-promoting substances are, for example, DMSO, spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils and copolymers thereof with polyethers, fatty acid esters, triglycerides, fatty alcohols.

Suitable antioxidants are sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole, tocopherol.

Suitable light stabilizers are, for example, novantisolic acid.

Suitable adhesives are, for example, cellulose derivatives, starch derivatives, polyacrylates, natural polymers such as alginates, gelatin.

Emulsions can be administered orally, dermally or as injections.

Emulsions are either of the water-in-oil type or of the oil-in-water type.

They are prepared by dissolving the active compound either in the hydrophobic or in the hydrophilic phase and homogenizing this with the solvent of the other phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries such as colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-enhancing substances.

Suitable hydrophobic phases (oils) are:

liquid paraffins, silicone oils, natural vegetable oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as caprylic/capric biglyceride, triglyceride mixture with vegetable fatty acids of the chain length C8-C12 or other specially selected natural fatty acids, partial glyceride mixtures of saturated or unsaturated fatty acids possibly also containing hydroxyl groups, mono- and diglycerides of the C8-C10 fatty acids, fatty acid esters such as ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol perlargonate, esters of a branched fatty acid of medium chain length with saturated fatty alcohols of chain length C16-C18, isopropyl myristate, isopropyl palmitate, caprylic/capric acid esters of saturated fatty alcohols of chain length C12-C18, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid esters such as synthetic duck coccygeal gland fat, dibutyl phthalate, diisopropyl adipate, and ester mixtures related to the latter,

fatty alcohols such as isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol, and

fatty acids such as oleic acid and

mixtures thereof.

Suitable hydrophilic phases are: water, alcohols such as propylene glycol, glycerol, sorbitol and mixtures thereof.

Suitable emulsifiers are:

non-ionic surfactants, e.g. polyethoxylated castor oil, polyethoxylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether;

ampholytic surfactants such as di-sodium N-lauryl-p-iminodipropionate or lecithin;

anionic surfactants, such as sodium lauryl sulfate, fatty alcohol ether sulfates, mono/dialkyl polyglycol ether orthophosphoric acid ester monoethanolamine salt;

cation-active surfactants, such as cetyltrimethylammonium chloride.

Suitable further auxiliaries are: substances which enhance the viscosity and stabilize the emulsion, such as carboxymethylcellulose, methylcellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycols, waxes, colloidal silicic acid or mixtures of the substances mentioned.

Suspensions can be administered orally or topically/dermally. They are prepared by suspending the active compound in a suspending agent, if appropriate with addition of other auxiliaries such as wetting agents, colorants, bioabsorption-promoting substances, preservatives, antioxidants, light stabilizers.

Liquid suspending agents are all homogeneous solvents and solvent mixtures.

Suitable wetting agents (dispersants) are the emulsifiers given above.

Other auxiliaries which may be mentioned are those given above.

Semi-solid preparations can be administered orally or topically/dermally. They differ from the suspensions and emulsions described above only by their higher viscosity.

For the production of solid preparations, the active compound is mixed with suitable excipients, if appropriate with addition of auxiliaries, and brought into the desired form.

Suitable excipients are all physiologically tolerable solid inert substances. Those used are inorganic and organic substances. Inorganic substances are, for example, sodium chloride, carbonates such as calcium carbonate, hydrogencarbonates, aluminium oxides, titanium oxide, silicic acids, argillaceous earths, precipitated or colloidal silica, or phosphates. Organic substances are, for example, sugar, cellulose, foodstuffs and feeds such as milk powder, animal meal, grain meals and shreds, starches.

Suitable auxiliaries are preservatives, antioxidants, and/or colorants which have been mentioned above.

Other suitable auxiliaries are lubricants and glidants such as magnesium stearate, stearic acid, talc, bentonites, disintegration-promoting substances such as starch or crosslinked polyvinylpyrrolidone, binders such as starch, gelatin or linear polyvinylpyrrolidone, and dry binders such as microcrystalline cellulose.

In general, “parasiticidally effective amount” means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The parasiticidally effective amount can vary for the various compounds/compositions used in the invention. A parasiticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired parasiticidal effect and duration, target species, mode of application, and the like.

The compositions which can be used in the invention can comprise generally from about 0.001 to 95% of the compound of formula I and/or of an acceptable salts thereof.

Generally, it is favorable to apply the compounds of formula I and/or an acceptable salts thereof in total amounts of 0.5 mg/kg to 100 mg/kg per day, preferably 1 mg/kg to 50 mg/kg per day.

Ready-to-use preparations contain the compounds of the formula I, acting against parasites, preferably ectoparasites, and/or an acceptable salts thereof, in concentrations of 10 ppm to 80 percent by weight, preferably from 0.1 to 65 percent by weight, more preferably from 1 to 50 percent by weight, most preferably from 5 to 40 percent by weight.

Preparations which are diluted before use contain the compounds of the formula I, acting against ectoparasites, and/or an acceptable salts thereof, in concentrations of 0.5 to 90 percent by weight, preferably of 1 to 50 percent by weight.

Furthermore, the preparations comprise the compounds of formula I and/or an acceptable salts thereof against endoparasites in concentrations of 10 ppm to 2 per cent by weight, preferably of 0.05 to 0.9 percent by weight, very particularly preferably of 0.005 to 0.25 percent by weight.

In a preferred embodiment of the present invention, the compositions comprising the compounds of formula I and/or an acceptable salts thereof are applied dermally/topically.

In a further preferred embodiment, the topical application is conducted in the form of compound-containing shaped articles such as collars, medallions, ear tags, bands for fixing at body parts, and adhesive strips and foils.

Generally, it is favorable to apply solid formulations which release compounds of formula I and/or an acceptable salts thereof in total amounts of 10 mg/kg to 300 mg/kg, preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg to 160 mg/kg body weight of the treated animal in the course of three weeks.

For the preparation of the shaped articles, thermoplastic and flexible plastics as well as elastomers and thermoplastic elastomers are used. Suitable plastics and elastomers are polyvinyl resins, polyurethane, polyacrylate, epoxy resins, cellulose, cellulose derivatives, polyamides and polyester which are sufficiently compatible with the compounds of formula I. A detailed list of plastics and elastomers as well as preparation procedures for the shaped articles is given e.g. in WO 03/086075.

Compositions to be used according to this invention may also contain other active ingredients, for example other pesticides, insecticides, herbicides, fungicides, other pesticides, or bactericides, fertilizers such as ammonium nitrate, urea, potash, and super-phosphate, phytotoxicants and plant growth regulators, safeners and nematicides. These additional ingredients may be used sequentially or in combination with the above-described compositions, if appropriate also added only immediately prior to use (tank mix). For example, the plant(s) may be sprayed with a composition of this invention either before or after being treated with other active ingredients.

These agents can be admixed with the agents used according to the invention in a weight ratio of 1:10 to 10:1. Mixing the compounds of the formula I and/or an acceptable salts thereof or the compositions comprising them in the use form as pesticides with other pesticides frequently results in a broader pesticidal spectrum of action.

The following list of pesticides A (hereinafter also mixing partner A) together with which the compounds of the formula I and/or an acceptable salts thereof can be used and with which potential synergistic effects might be produced, is intended to illustrate the possible combinations, but not to impose any limitation:

-   A.1. Organo(thio)phosphates: acephate, azamethiphos, azinphos-ethyl,     azinphos-methyl, chlorethoxyfos, chlorfenvinphos, chlormephos,     chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos,     demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos,     dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos,     famphur, fenamiphos, fenitrothion, fenthion, flupyrazophos,     fosthiazate, heptenophos, isoxathion, malathion, mecarbam,     methamidophos, methidathion, mevinphos, monocrotophos, naled,     omethoate, oxydemeton-methyl, parathion, parathion-methyl,     phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,     pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos,     pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos,     terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon,     vamidothion; -   A.2. Carbamates: aldicarb, alanycarb, bendiocarb, benfuracarb,     butocarboxim, butoxy-carboxim, carbaryl, carbofuran, carbosulfan,     ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb,     methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur,     thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb, triazamate; -   A.3. Pyrethroids: acrinathrin, allethrin, d-cis-trans allethrin,     d-trans allethrin, bifenthrin, bioallethrin, bioallethrin     S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin,     beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin,     cypermethrin, alpha-cypermethrin, beta-cypermethrin,     theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin,     empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate,     flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin,     permethrin, phenothrin, prallethrin, resmethrin, RU 15525,     silafluofen, tefluthrin, tetramethrin, tralomethrin, transfluthrin,     ZXI 8901; -   A.4. Juvenile hormone mimics: hydroprene, kinoprene, methoprene,     fenoxycarb, pyriproxyfen; -   A.5. Nicotinic receptor agonists/antagonists compounds: acetamiprid,     bensultap, cartap hydrochloride, clothianidin, dinotefuran,     imidacloprid, thiamethoxam, nitenpyram, nicotine, spinosad     (allosteric agonist), thiacloprid, thiocyclam, thiosultap-sodium and     AKD1022. -   A.6. GABA gated chloride channel antagonist compounds: chlordane,     endosulfan, gamma-HCH (lindane); acetoprole, ethiprole, fipronil,     pyrafluprole, pyriprole, vaniliprole, the phenylpyrazole compound of     formula A6.1

-   A.7. Chloride channel activators: abamectin, emamectin benzoate,     milbemectin, lepimectin; -   A.8. METI I compounds: fenazaquin, fenpyroximate, pyrimidifen,     pyridaben, tebufenpyrad, tolfenpyrad, flufenerim, rotenone; -   A.9. METI II and III compounds: acequinocyl, fluacyprim,     hydramethylnon; -   A.10. Uncouplers of oxidative phosphorylation: chlorfenapyr, DNOC; -   A.11. Inhibitors of oxidative phosphorylation: azocyclotin,     cyhexatin, diafenthiuron, fenbutatin oxide, propargite, tetradifon; -   A.12. Moulting disruptors: cyromazine, chromafenozide, halofenozide,     methoxyfenozide, tebufenozide; -   A.13. Synergists: piperonyl butoxide, tribufos; -   A.14. Sodium channel blocker compounds: indoxacarb, metaflumizone; -   A.15. Fumigants: methyl bromide, chloropicrin sulfuryl fluoride; -   A.16. Selective feeding blockers: crylotie, pymetrozine, flonicamid; -   A.17. Mite growth inhibitors: clofentezine, hexythiazox, etoxazole; -   A.18. Chitin synthesis inhibitors: buprofezin, bistrifluron,     chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron,     hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron,     triflumuron; -   A.19. Lipid biosynthesis inhibitors: spirodiclofen, spiromesifen,     spirotetramat; -   A.20. Octapaminergic agonsits: amitraz; -   A.21. Ryanodine receptor modulators: flubendiamide; -   A.22. Various: aluminium phosphide, amidoflumet, benclothiaz,     benzoximate, bifenazate, borax, bromopropylate, cyanide,     cyenopyrafen, cyflumetofen, chinomethionate, dicofol, fluoroacetate,     phosphine, pyridalyl, pyrifluquinazon, sulfur, organic sulphur     compounds, tartar emetic and sulfoximine compounds A22.1, A22.2 or     A22.3:

pyrimidinyl alkynylether compounds A22.4 or thiadiazolyl alkynylether compounds A22.5,

wherein R^(A-22) is methyl or ethyl and Het* is 3,3-dimethylpyrrolidin-1-yl, 3-methylpiperidin-1-yl, 3,5-dimethylpiperidin-1-yl, 3-trifluormethylpiperidin-1-yl, hexahydroazepin-1-yl, 2,6-dimethylhexahydroazepin-1-yl or 2,6-dimethylmorpholin-4-yl;

-   A.23.     N—R′-2,2-dihalo-1-R″cyclo-propanecarboxamide-2-(2,6-dichloro-α,α,α-tri-fluoro-p-tolyl)hydrazone     or     N—R′-2,2-di(R′″)propionamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)-hydrazone,     wherein R′ is methyl or ethyl, halo is chloro or bromo, R″ is     hydrogen or methyl and R′″ is methyl or ethyl; -   A.24. Anthranilamides: chloranthraniliprole, the compound of formula     A24.1

-   A.25. Malononitrile compounds: CF₂HCF₂CF₂CF₂CH₂C(CN)₂CH₂CH₂CF₃,     (2-(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(3,3,3-trifluoro-propyl)malononitrile),     CF₃(CH₂)₂C(CN)₂CH₂(CF₂)₅CF₂H,     (2-(2,2,3,3,4,4,5,5,6,6,7,7-Dodecafluoroheptyl)-2(3,3,3-trifluoro-propyl)-malononitrile),     CF₃(CH₂)₂C(CN)₂(CH₂)₂C(CF₃)₂F(2-(3,4,4,4-Tetrafluoro-3-trifluoromethyl-butyl)-2-(3,3,3-trifluoro-propyl)-malononitrile),     CF₃(CH₂)₂C(CN)₂(CH₂)₂(CF₂)₃CF₃(2-(3,3,4,4,5,5,6,6,6-Nonafluoro-hexyl)-2-(3,3,3-trifluoro-propyl)-malononitrile),     CF₂H(CF₂)₃CH₂C(CN)₂CH₂(CF₂)₃CF₂H     (2,2-Bis-(2,2,3,3,4,4,5,5-octafluoro-pentyl)-malononitrile),     CF₃(CH₂)₂C(CN)₂CH₂(CF₂)₃CF₃(2-(2,2,3,3,4,4,5,5,5-Nonafluoro-pentyl)-2-(3,3,3-trifluoro-propyl)-malononitrile),     CF3(CF₂)₂CH₂C(CN)₂CH₂(CF₂)3CF₂H(2-(2,2,3,3,4,4,4-Heptafluoro-butyl)-2-(2,2,3,3,4,4,5,5-octafluoro-pentyl)-malononitrile),     CF₃CF₂CH₂C(CN)₂CH₂(CF₂)₃CF₂H(2-(2,2,3,3,4,4,5,5-Octafluoro-pentyl)-2-(2,2,3,3,3-pentafluoro-propyl)-malononitrile),     CF₂HCF₂CF₂CF₂CH₂C(CN)₂CH₂CH₂CF₂CF₃(2-(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(3,3,4,4,4-pentafluorobutyl)-malonodinitrile),     CF₃(CH₂)₂C(CN)₂CH₂(CF₂)₃CF₂H(2-(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(3,3,3-trifluoro-butyl)-malononitrile); -   A.26. Microbial disruptors: Bacillus thuringiensis subsp.     Israelensi, Bacillus sphaericus, Bacillus thuringiensis subsp.     Aizawai, Bacillus thuringiensis subsp. Kurstaki, Bacillus     thuringiensis subsp. Tenebrionis.

The commercially available compounds of the group A may be found in The Pesticide Manual, 13th Edition, British Crop Protection Council (2003) among other publications.

Thioamides of formula A6.1 and their preparation have been described in WO 98/28279. Lepimectin is known from Agro Project, PJB Publications Ltd, November 2004. Benclothiaz and its preparation have been described in EP-A1 454621. Methidathion and Paraoxon and their preparation have been described in Farm Chemicals Handbook, Volume 88, Meister Publishing Company, 2001. Acetoprole and its preparation have been described in WO 98/28277. Metaflumizone and its preparation have been described in EP-A1 462 456. Flupyrazofos has been described in Pesticide Science 54, 1988, p. 237-243 and in U.S. Pat. No. 4822779. Pyrafluprole and its preparation have been described in JP 2002193709 and in WO 01/00614. Pyriprole and its preparation have been described in WO 98/45274 and in U.S. Pat. No. 6335357. Amidoflumet and its preparation have been described in U.S. Pat. No. 6221890 and in JP 21010907. Flufenerim and its prepara-tion have been described in WO 03/007717 and in WO 03/007718. AKD 1022 and its preparation have been described in U.S. Pat. No. 6300348. Chloranthraniliprole has been described in WO 01/70671, WO 03/015519 and WO 05/118552. Anthranilamide deriva-tives of formula M24.1 have been described in WO 01/70671, WO 04/067528 and WO 05/118552. Cyflumetofen and its preparation have been described in WO 04/080180. The aminoquinazolinone compound pyrifluquinazon has been described in EP A 109 7932. Sulfoximine derivatives of formulae M22.1, M22.2 or M22.3 or in analogy thereof and their preparation methods have been described in WO 2006/060029. The alkynylether compounds M22.4 and M22.5 are described e.g. in JP 2006131529. Organic sulfur compounds have been described in WO 2007060839. The malononitrile compounds have been described in WO 02/089579, WO 02/090320, WO 02/090321, WO 04/006677, WO 05/068423, WO 05/068432 and WO 05/063694.

Fungicidal mixing partners are those selected from the group consisting of acylalanines such as benalaxyl, metalaxyl, ofurace, oxadixyl,

amine derivatives such as aldimorph, dodine, dodemorph, fenpropimorph, fenpropidin, guazatine, iminoctadine, spiroxamin, tridemorph,

anilinopyrimidines such as pyrimethanil, mepanipyrim or cyrodinyl,

antibiotics such as cycloheximid, griseofulvin, kasugamycin, natamycin, polyoxin or streptomycin,

azoles such as bitertanol, bromoconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquiconazole, flusilazole, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole, prochloraz, prothioconazole, tebuconazole, triadimefon, triadimenol, triflumizol, triticonazole, flutriafol, dicarboximides such as iprodion, myclozolin, procymidon, vinclozolin, dithiocarbamates such as ferbam, nabam, maneb, mancozeb, metam, metiram, propineb, polycarbamate, thiram, ziram, zineb,

heterocyclic compounds such as anilazine, benomyl, boscalid, carbendazim, carboxin, oxycarboxin, cyazofamid, dazomet, dithianon, famoxadon, fenamidon, fenarimol, fuberidazole, flutolanil, furametpyr, isoprothiolane, mepronil, nuarimol, probenazole, proquinazid, pyrifenox, pyroquilon, quinoxyfen, silthiofam, thiabendazole, thifluzamid, thiophanate-methyl, tiadinil, tricyclazole, triforine,

copper fungicides such as Bordeaux mixture, copper acetate, copper oxychloride, basic copper sulfate,

nitrophenyl derivatives such as binapacryl, dinocap, dinobuton, nitrophthalisopropyl, phenylpyrroles such as fenpiclonil or fludioxonil,

sulfur,

other fungicides such as acibenzolar-S-methyl, benthiavalicarb, carpropamid, chlorothalonil, cyflufenamid, cymoxanil, diclomezin, diclocymet, diethofencarb, edifenphos, ethaboxam, fenhexamid, fentin-acetate, fenoxanil, ferimzone, fluazinam, fosetyl, fosetyl-aluminum, iprovalicarb, hexachlorobenzene, metrafenon, pencycuron, propamocarb, phthalide, toloclofos-methyl, quintozene, zoxamid,

strobilurins such as azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin or trifloxystrobin,

sulfenic acid derivatives such as captafol, captan, dichlofluanid, folpet, tolylfluanid, cinnemamides and analogs such as dimethomorph, flumetover or flumorph.

The animal pest, i.e. arthropodes and nematodes, the plant, soil or water in which the plant is growing can be contacted with the present compound(s) of the formula I and/or an agriculturally acceptable salt thereof or composition(s) containing them by any application method known in the art. As such, “contacting” in-cludes both direct contact (applying the compounds/compositions directly on the animal pest or plant—typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the animal pest or plant).

Moreover, animal pests may be controlled by contacting the target pest, its food supply, habitat, breeding ground or its locus with a pesticidally effective amount of compounds of formula I and/or an agriculturally acceptable salt thereof. As such, the application may be carried out before or after the infection of the locus, growing crops, or harvested crops by the pest.

“Locus” means a habitat, breeding ground, plant, in particular cultivated plant, plant propagation material such as seed, soil, area, material or environ-ment in which a pest or parasite is growing or may grow.

In general “pesticidally effective amount” means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The pesticidally effective amount can vary for the various compounds/compositions used in the invention. A pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.

The compounds of formula I, the agriculturally acceptable salt thereof and their compositions can be used for protecting wooden materials such as trees, board fences, sleepers, etc. and buildings such as houses, outhouses, factories, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants and/or termites, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities). The compounds of are applied not only to the surrounding soil surface or into the underfloor soil in order to protect wooden materials but it can also be applied to lumbered articles such as surfaces of the under-floor concrete, al-cove posts, beams, plywoods, furniture, etc., wooden articles such as particle boards, half boards, etc. and vinyl articles such as coated electric wires, vinyl sheets, heat insu-lating material such as styrene foams, etc. In case of application against ants doing harm to crops or human beings, the ant controller of the present invention is applied to the crops or the surrounding soil, or is directly applied to the nest of ants or the like.

The compounds of the invention can also be applied preventively to places at which occurrence of the pests is expected.

The compounds of formula I and/or an agriculturally acceptable salt thereof may also be used to protect growing plants from attack or infestation by pests by contacting the plant with a pesticidally effective amount of compounds of formula I and/or an agriculturally acceptable salt thereof. As such, “contacting” includes both direct contact (applying the compounds/compositions directly on the pest and/or plant—typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus of the pest and/or plant).

In the case of soil treatment or of application to the pests dwelling place or nest, the quantity of active ingredient (i.e. compounds of the formula I and/or an agriculturally acceptable salt thereof or mixtures thereof with mixing partner A) ranges from 0.0001 to 500 g per 100 m², preferably from 0.001 to 20 g per 100 m².

Customary application rates in the protection of materials are, for example, from 0.01 g to 1000 g of active compound (i.e. compounds of the formula I and/or an agriculturally acceptable salt thereof or mixtures thereof with mixing partner A) per m² treated material, desirably from 0.1 g to 50 g per m².

Insecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95% by weight, preferably from 0.1 to 45% by weight, and more preferably from 1 to 25% by weight of at least one repellent and/or insecticide (i.e. compounds of the formula I and/or an agriculturally acceptable salt thereof or mixtures thereof with mixing partner A).

For use in bait compositions, the typical content of active ingredient (i.e. compounds of the formula I and/or an agriculturally acceptable salt thereof or mixtures thereof with mixing partner A) is from 0.001% by weight to 15% by weight, desirably from 0.001% by weight to 5% by weight of active compound.

For use in spray compositions, the content of active ingredient (i.e. compounds of the formula I and/or an agriculturally acceptable salt thereof or mixtures thereof with mixing partner A) is from 0.001 to 80% by weight, preferably from 0.01 to 50% by weight and most preferably from 0.01 to 15% by weight.

For use in treating crop plants, the rate of application of the active ingredients (i.e. compounds of the formula I and/or an agriculturally acceptable salt thereof or mixtures thereof with mixing partner A) may be in the range of 0.1 g to 4000 g per hectare, desirably from 25 g to 600 g per hectare, more desirably from 50 g to 500 g per hectare.

In the treatment of seed, the application rates of the compounds of the present invention or mixture with mixing partners A are generally from 0.1 g to 10 kg per 100 kg of plant propagation material such as seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 200 g per 100 kg of plant propagation material such as seed.

The present invention is now illustrated in further detail by the following examples.

PREPARATION EXAMPLES Example 1 Preparation of 1-(3-prop-2-ynyl-thiazolidin-2-ylidene)amino-1-(2,3-dichlorophenyl)-2-(3,5-dimethylphenyl)-ethane (compound 1)

A mixture of 1-(4,5-dihydrothiazol-2-yl)-amino-1-(2,3-dichlorophenyl)-2-(3,5-dimethylphenyl)-ethane (150 mg), potassium carbonate (80 mg) and dimethyl formamide (DMF, 10 ml) was heated up to 60° C. and a solution of propargyl bromide (57 mg) in DMF (2 ml) was added. Stirring was continued for 4 h at the same temperature and continued at room temperature overnight. Aqueous work-up by dilution in ethyl acetate, washing with an aqueous potassium carbonate solution (5% strenght) and water and drying over sodium sulphate yielded a crude product that was purified by column chromatography over silica gel to give 13 mg of the title compound.

¹H-NMR (CDCl₃): δ=2.25 (s), 2.75-3.05 (m), 3.45 (mc), 4.25 (s), 4.65 (mc), 6.8 (mc), 7.1-7.55 ppm (m).

Example 2 Preparation of 1-{3-[3-(tetrahydropyran-2-yloxy)propyl]thiazolidin-2-ylidene}amino-1-(2,3-dichlorophenyl)-2-(3,5-dimethylphenyl)-ethane (compound 2)

A mixture of 1-(4,5-dihydrothiazol-2-yl)amino-1-(2,3-dichlorophenyl)-2-(3,5-dimethylphenyl)-ethane (300 mg), potassium tert.-butanolate and tetrahydrofuran (THF, 10 ml) was treated at room temperature with 2-(3-bromo-propoxy)-tetrahydropyran (210 mg) for 3 days. Aqueous work-up by dilution in ethyl acetate, washing with an aqueous potassium carbonate solution (5% strength) and water and drying over sodium sulphate yielded a crude product that was purified by column chromatography over silica gel to give 200 mg of the title compound.

¹H-NMR (CDCl₃): δ=1.45-1.95 (m), 2.25 (s), 2.3 (d), 2.7 (mc), 3.0 (mc), 3.35-3.6 (m), 3.85 (mc), 4.55-4.7 (mc), 6.75 (s), 6.8 (s), 7.1 (t), 7.4 (mc), 7.5 ppm (mc).

Example 3 Preparation of 1-(4,5,4′,5′-tetrahydro-[2,3]-bithiazolyl-2′-ylidene)amino-1-(2,2-difluoro-benzo[1,3]dioxol-4-yl)-2-(3,5-dimethyl-phenyl)-ethane (compound 3)

A solution of 1-amino-1-(2,2-difluoro-benzo[1,3]dioxol-4-yl)-2-(3,5-dimethylphenyl)-ethane (0.39 g) in diethyl ether was treated at 0° C. with 2-chloroethyl isothiocyanate (0.16 g) and stirring was continued for 5 h at this temperature. The mixture was quenched with an aqueous sodium hydroxide solution (1 M, 4 ml) and water (15 ml) and stirred for 15 minutes. The organic phase was washed with water, the aqueous phase was extracted with diethyl ether, the combined organic phases were dried over sodium sulphate and the solvent was removed in vacuo. The remainder was purified by column chromatography to yield 0.1 g of the title compound.

¹H-NMR (CDCl₃): δ=2.2 (s), 3.0-3.3 (m), 4.0 (mc), 4.2 (mc), 4.55 (mc), 6.7 (s), 6.8 (s), 6.9 (mc), 7.05 (mc), 7.3 ppm (mc).

Example 4 Preparation of 2-[1-(2,3-dichlorophenyl)-2-(3,5-dimethylphenyl)ethylimino]-thiazolidine-3-carbothioic acid (3-trifluoromethylphenyl)amide (compound 4)

A solution of 1-(4,5-dihydrothiazol-2-yl)amino-1-(2,3-dichlorophenyl)-2-(3,5-dimethylphenyl)-ethane (0.25 g) in chloroform (10 ml) was treated with 1-isothiocyanato-3-trifluoromethylbenzene (0.13 g) at room temperature overnight. The solvent was evaporated in vacuo and the remainder was purified by column chromatography to yield 0.20 g of the title compound.

¹H-NMR (CDCl₃): δ=2.1 (s), 2.85-3.2 (m), 4.55 (mc), 4.9 (mc), 5.0 (mc), 6.65 (s), 6.8 (s), 7.1-7.75 (m), 14.6 ppm (s).

Example 5 Preparation of 1-[3-(toluene-4-sulfonyl)thiazolidin-2-ylidene]-amino-1-(2,3-Dimethyl-phenyl)-2-(3-tolyl)-ethane (compound 5)

A solution of 1-(4,5-dihydro-3H-thiazol-2-yl)amino-1-(2,3-dimethyl-phenyl)-2-(3-tolyl)-ethane (0.20 g) in THF (20 ml) was treated with potassium tert.-butanolate (0.10 g) and 4-methylbenzenesulfonyl chloride (0.14 g) and the mixture was stirred for 2 h at room temperature. Aqueous work-up by dilution in ethyl acetate, washing with an aqueous potassium carbonate solution (5% strenght) and water and drying over sodium sulphate yielded a crude product that was purified by column chromatography over silica gel to give 0.20 g of the title compound. Melting point: 141.0-144.0° C.

The compounds of formula I′.1 shown in table 2 hereinafter (examples 6 to 21)

have been prepared in analogy to the preparation examples shown hereinbefore.

TABLE 2 Physico-chemical data (m.p [° C.], ¹H-NMR Ex. X R¹ R² R³ R⁴ R⁵ R⁶ (CDCl₃) [ppm]) 6 S

H H H Cl H δ = 2.95-3.15 (m), 3.95 (mc), 4.25 (mc), 4.75 (mc), 5.3 (d), 5.5 (d), 6.0 (mc), 6.9-7.3 (m) 7 S

H H H Cl H 104.0-106.0 8 O

H H H Cl H 2.95 (mc), 3.75-4.15 (m), 4.7-4.85 (m), 5.3 (d), 5.5 (d), 6.0 (mc), 6.95-7.4 (m) 9 S

CH₃ CH₃ H CH₃ CH₃ 2.15 (s), 2.25 (s), 2.30 (s), 2.9-3.15 (m), 4.5 (mc), 4.7 (mc), 4.85 (mc), 6.65 (s), 6.8 (s), 7.05-7.4 (m), 7.55 (s) 10 S

Cl Cl H CH₃ CH₃ 2.25 (s), 2.5 (mc), 2.75 (mc), 3.15 (mc), 4.0 (mc), 4.2 (mc), 4.75 (mc), 6.45 (mc), 6.55 (s), 7.05 (t), 7.3 (d), 8.9 (s), 8.65 (s), 8.75 (s) 11 S

Cl Cl H CH₃ CH₃ 148.0-149.0 12 S

Cl Cl H CH₃ CH₃ 2.25 (s), 2.45 (mc), 2.75 (mc), 3.15 (mc), 4.0 (mc), 4.2 (mc), 4.65 (mc), 6.45 (mc), 6.55 (s), 6.8 (s), 6.95 (t), 8.7 (s), 8.8 (s) 13 S

Cl Cl H CH₃ CH₃ 50.0-52.0 14 S

Cl Cl H CH₃ CH₃ 2.2 (s), 2.45 (s), 2.65 (mc), 2.9-3.1 (m), 3.9 (mc), 4.15 (mc), 4.45 (mc), 6.45 (s), 6.8 (s), 7.1 (mc), 7.2-7.35 (m), 7.95 (d) 15 S

Cl Cl H CH₃ CH₃ 52.0-55.0 16 S

CH₃ CH₃ H CH₃ CH₃ 140.0-145.0 17 S

Cl Cl H CH₃ CH₃ 136.0-143.0 18 S

CH₃ CF₃ H CH₃ CH₃ 2.20 (s), 2.45 (s), 2.8 (mc), 3.1 (mc), 4.0- 4.35 (m), 6.45 (s), 6.8 (s), 7.15 (mc), 7.25- 7.5 (m), 7.95 (d) 19 S

Cl Cl H CH₃ CH₃ 2.25 (s), 2.4-2.7 (mc), 3.0-3.15 (m), 3.7 (s), 3.95-4.45 (m), 4.65 (mc), 6.4-7.4 (m) 20 S

Cl Cl H CH₃ CH₃ 2.1 (s), 2.4 (s), 2.7- 3.15 (m), 4.5 (mc), 4.8-4.95 (m), 6.65 (s), 6.8 (s), 7.15-7.4 (m), 14.3 (s) 21 S

CH₃ CH₃ H CH₃ H 1.5-1.75 (m), 2.15- 2.35 (m), 3.0 (mc), 3.9 (mc), 4.1 (mc), 4.7 (mc), 6.15-6.4 (m), 6.75-7.4 (m)

Action Against Pests:

I. Cotton aphid (Aphis gossypi)

The active compounds were formulated in 50:50 acetone:water and 100 ppm Kinetic® surfactant.

Cotton plants in the cotyledon stage (variety ‘Delta Pine’) are infested with approximately 100 laboratory-reared aphids by placing infested leaf sections on top of the test plants. The leaf sections are removed after 24 hours. The cotyledons of the intact plants are dipped into gradient solutions of the test compound. Aphid mortality on the treated plants, relative to mortality on check plants, is determined after 5 days.

In this test, the compounds of examples 1 to 4, 6, 8 to 11 and 13 to 21 at 300 ppm showed over 70% mortality in comparison with untreated controls.

II. Green Peach Aphid (Myzus persicae)

The active compounds were formulated in 50:50 acetone:water and 100 ppm Kinetic® surfactant.

Pepper plants in the 2^(nd) leaf-pair stage (variety ‘California Wonder’) are infested with approximately 40 laboratory-reared aphids by placing infested leaf sections on top of the test plants. The leaf sections are removed after 24 hours. The leaves of the intact plants are dipped into gradient solutions of the test compound. Aphid mortality on the treated plants, relative to mortality on check plants, is determined after 5 days.

In this test, the compounds of examples 1 to 4, 6 to 11 and 13 to 21 at 300 ppm showed over 70% mortality in comparison with untreated controls.

III. Silverleaf Whitefly

The active compounds were formulated in 50:50 acetone:water and 100 ppm Kinetic® surfactant.

Selected cotton plants were grown to the cotyledon state (one plant per pot). The cotyledons were dipped into the test solution to provide complete coverage of the foliage and placed in a well-vented area to dry. Each pot with treated seedling was placed in a plastic cup and 10 to 12 whitefly adults (approximately 3-5 day old) were introduced. The insects were colleted using an aspirator and an 0.6 cm, non-toxic Tygon® tubing (R-3603) connected to a barrier pipette tip. The tip, containing the collected insects, was then gently inserted into the soil containing the treated plant, allowing insects to crawl out of the tip to reach the foliage for feeding. The cups were covered with a re-usable screened lid (150 micron mesh polyester screen PeCap from Tetko Inc). Test plants were maintained in the holding room at about 25° C. and 20-40% relative humid-ity for 3 days avoiding direct exposure to the fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the cup. Mortality was assessed 3 days after treatment of the plants.

In this test, the compounds of examples 1 to 4, 8 to 11, 13 to 17 and 19 to 21 at 300 ppm showed over 70% mortality in comparison with untreated controls.

IV. COMPARATIVE EXAMPLES Comparative Example 1 Action Against Silverleaf Whitefly

The action against silverleaf whitefly of the inventive compounds from preparation examples 1 and 4 has been compared with the action of compound C.3, wherein R¹ is hydrogen (not in accordance with the present invention)

by evaluation of the test shown in paragraph III.). The results are compiled in table 3.

TABLE 3 mortality in comparison concentration with untreated controls [%] [ppm] compound C.3 compound 1 compound 4 300 100 100 100 100 100 100 100 10 0 100 50 

1. A compound of formula (I′)

wherein A is a radical of formulae A.1 or A.2

wherein # denotes the bond to the remaining compound of formula (I′) X is selected from the group consisting of O, S and NR^(X), wherein R^(X) is selected from the group consisting of hydrogen, cyano, nitro, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl, C₁-C₃-haloalkoxy, formyl, C₁-C₆-alkylcarbonyl and C₁-C₆-alkoxycarbonyl; R1 is selected from the group consisting of —C(═S)—NR^(B1)R^(B2), C₂-C₈-alkenyl, C₂-C₈-alkynyl and C₃-C₈-cycloalkyl, wherein the three last mentioned groups are unsubstituted or may carry 1 to 4 substituents R^(1e), B is linear or branched C₁-C₄-alkanediyl, which is unsubstituted or may carry 1, 2, 3 or 4 radicals selected from the group consisting of halogen and C₁-C₃-alkoxy; R^(A) is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the last three mentioned radicals may carry 1, 2, 3 or 4 substituents selected independently from the group consisting of halogen, C₁-C₃-alkoxy, C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio and C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1e), naphthyl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1f), and hetaryl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1h); R^(B1), R^(B2) are selected independently from the group consisting of hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the last three mentioned radicals may carry 1, 2, 3 or 4 substituents selected independently from the group consisting of halogen, C₁-C₃-alkoxy, C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio and C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1e), phenyl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1f), naphthyl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1f), and hetaryl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1h); R^(B2)′ is selected from the group consisting of C₃-C₈-cycloalkyl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1e), phenyl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1f), naphthyl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1f), and hetaryl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1h); R^(C) is selected from the group consisting of C₁-C₆-alkyl which carries 1, 2, 3 or 4 radicals selected from the group consisting of C(═O)OH, aryloxy, hetaryloxy, arylthio, hetarylthio and C₁-C₄-alkoxycarbonyl, wherein the five last mentioned radicals are unsubstituted or may carry 1, 2, 3 or 4 groups selected independently from the group consisting of CN, NO₂, halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl, C₁-C₃-haloalkoxy and C₃-C₈-cycloalkyl; R^(C)′ is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the last three mentioned radicals may carry 1, 2, 3 or 4 substituents selected independently from the group consisting of halogen, C₁-C₃-alkoxy, C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio and C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1e), phenyl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1f), naphthyl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1f), and hetaryl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1h); R^(D), R^(E) are selected from the group consisting of C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the last two mentioned radicals may carry 1, 2, 3 or 4 substituents selected independently from the group consisting of halogen, C₁-C₃-alkoxy, C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio and C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1e), phenyl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1f), naphthyl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1f), and hetaryl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1h); R^(D)′, R^(E)′, R^(F), R^(G), R^(H1), R^(H2) have one of the meanings given for R^(D), R^(E) or are selected from the group consisting of hydrogen and C₁-C₆-alkyl, which is unsubstituted or carries 1, 2, 3 or 4 substituents selected independently from the group consisting of halogen, C₁-C₃-alkoxy, C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio and C₃-C₈-cycloalkyl; R^(I), R^(K) are selected from the group consisting of C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the last three mentioned radicals may carry 1, 2, 3 or 4 substituents selected independently from the group consisting of halogen, C₁-C₃-alkoxy, C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio and C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1e), phenyl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1f), naphthyl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1f), and hetaryl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1h); R^(J) is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, wherein the last three mentioned radicals may carry 1, 2, 3 or 4 substituents selected independently from the group consisting of halogen, C₁-C₃-alkoxy, C₁-C₃-haloalkoxy, C₁-C₃-alkylthio, C₁-C₃-haloalkylthio and C₃-C₈-cycloalkyl, C₃-C₈-cycloalkyl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1e), phenyl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1f), naphthyl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1f), and hetaryl which is unsubstituted or may carry 1, 2, 3 or 4 substituents R^(1h); R^(1a), R^(1b), R^(1c) and R^(1d) is selected from the group consisting of hydrogen C₁-C₃-alkyl, C₁-C₃-alkoxy, C₃-C₈-cycloalkyl, C₂-C₃-alkenyl and C₂-C₃-alkenyloxy; R^(1e), R^(1g) are independently of one another selected from the group consisting of C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy; R^(1f), R^(1h) are independently of one another selected from the group consisting of CN, NO₂, halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl, C₁-C₃-haloalkoxy and C₃-C₈-cycloalkyl; R^(1i) is selected from the group consisting of hydrogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₃-C₈-cycloalkyl, C₂-C₃-alkenyl and C₂-C₃-alkenyloxy; and R^(1j) is selected from the group consisting of C₁-C₃-alkyl, C₁-C₃-alkoxy, C₃-C₈-cycloalkyl, C₂-C₃-alkenyl and C₂-C₃-alkenyloxy; and R², R³, R⁴, R⁵ and R⁶ are each independently hydrogen, halogen, OH, SH, NH₂, SO₃H, COOH, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylamino, di(C₁-C₆-alkyl)amino, C₁-C₈-alkylthio, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkenylamino, C₂-C₆-alkenylthio, C₂-C₆-alkynyl, C₂-C₆-alkynyloxy, C₂-C₆-alkynylamino, C₂-C₆-alkynylthio, C₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfoxyl, C₂-C₆-alkenylsulfonyl, C₂-C₆-alkynylsulfonyl, formyl, C₁-C₆-alkylcarbonyl, C₂-C₆-alkenylcarbonyl, C₂-C₆-alkynylcarbonyl, C₁-C₆-alkoxycarbonyl, C₂-C₆-alkenyloxycarbonyl, C₂-C₆-alkynyloxycarbonyl, C₁-C₆-alkylcarbonyloxy, C₁-C₆-alkylcarbonyloxy, C₂-C₆-alkenylcarbonyloxy, C₂-C₆-alkynylcarbonyloxy, wherein the carbon atoms in the aliphatic radicals of the aforementioned groups may carry any combination of 1, 2 or 3 radicals selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy and C₁-C₆-alkylthio, C(O)NR^(L)R^(M), (SO₂)NR^(L)R^(M), wherein R^(L) and R^(M) are each independently hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, or C₂-C₆-alkynyl, wherein the carbon atoms in these groups may carry any combination of 1, 2 or 3 radicals selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy and C₁-C₆-alkylthio, a radical Y—Ar or a radical Y-Cy, wherein Y is a single bond, oxygen, sulfur, C₁-C₆-alkanediyl or C₁-C₆-alkanediyloxy, Ar is phenyl, naphthyl or a mono- or bicyclic 5- to 10-membered heteroaromatic ring, which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen as ring members, wherein Ar is unsubstituted or may carry any combination of 1, 2, 3, 4 or 5 radicals selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy and C₁-C₆-alkylthio; and Cy is C₃-C₁₂-cycloalkyl, which is unsubstituted or substituted with any combination of 1, 2, 3, 4 or 5 radicals selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy and C₁-C₆-alkylthiol; and wherein two radicals R², R³, R⁴, R⁵ or R⁶ that are bound to adjacent carbon atoms of the phenyl rings may form together with said carbon atoms a fused benzene ring, a fused saturated or partially un-saturated 5-, 6-, or 7-membered carbocycle or a fused 5-, 6-, or 7-membered heterocycle, which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, S and N as ring members, and wherein the fused ring is unsubstituted or may carry any combination of 1, 2, 3, or 4 radicals selected from the group consisting of halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy and C₁-C₆-alkylthio; provided that R² and R³ are different from hydrogen or R² and R⁴ are different from hydrogen, the enantiomers, diastereomers or salts thereof.
 2. The compound of formula (I′) according to claim 1, wherein X is S.
 3. The compound of formula (I′) according to claim 1, wherein R¹ is —C(═S)—NR^(B1)R^(B2).
 4. The compound of formula (I′) according to claim 1, wherein R¹ is selected from the group consisting of C₂-C₈-alkenyl, C₂-C₈-alkynyl and C₃-C₈-cycloalkyl, which is unsubstituted or may carry 1 to 4 substituents R^(1e) as defined in claim
 1. 5. The compound of formula (I′) according to claim 1, wherein A is a radical of formula A.1.
 6. The compound according to claim 1, wherein R² is selected from the group consisting of hydrogen, halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy.
 7. The compound according to claim 1 wherein R² together with R³ forms a bivalent radical selected from —O—CH₂—O—, —O—CH₂—CH₂— or —O—CF₂—O—.
 8. The compound according to claim 1, wherein R³ is selected from the group consisting of hydrogen, halogen, C₁-C₃-alkyl and C₁-C₃-haloalkyl.
 9. The compound according to claim 1, wherein R⁴ is selected from the group consisting of hydrogen, halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy.
 10. The compound according to claim 1, wherein R⁵ is selected from the group consisting of hydrogen, halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy.
 11. The compound according to claim 1, wherein R⁶ is selected from the group consisting of halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy.
 12. The compound according to claim 1, wherein R⁷ is selected from the group consisting of hydrogen, halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy.
 13. The compound according to claim 1, wherein R² is selected from the group consisting of hydrogen, halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy; R³ is selected from the group consisting of hydrogen, halogen, C₁-C₃-alkyl and C₁-C₃-haloalkyl; or R² together with R³ forms a bivalent radical selected from —O—CH₂—CH_(2—), —O—CH₂—O— or —O—CF₂—O—; R⁴ is selected from the group consisting of hydrogen, halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy; R⁵ is selected from the group consisting of hydrogen, halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy; and R⁶ is selected from the group consisting of halogen, C₁-C₃-alkyl, C₁-C₃-alkoxy, C₁-C₃-haloalkyl and C₁-C₃-haloalkoxy; or the enantiomers, diastereomers or salts thereof.
 14. The compound according to claim 13, wherein A is a radical of formula A.1.
 15. The compound according to claim 14, wherein X is S.
 16. The compound according to claim 15, wherein R¹ is selected from the group consisting of C₂-C₈-alkenyl, C₂-C₈-alkynyl and C₃-C₈-cycloalkyl, which is unsubstituted or may carry 1 to 4 substituents R^(1e).
 17. The compound according to claim 15, wherein R² is selected from the group consisting of hydrogen, fluoro, chloro, bromo, methyl, methoxy, difluoromethyl, trifluoromethyl, difluoromethoxy and trifluoromethoxy.
 18. The compound according to claim 1, wherein R⁵ is selected from the group consisting of hydrogen, fluoro, chloro, bromo, methyl, methoxy, difluoromethyl, trifluoromethyl, difluoromethoxy and trifluoromethoxy.
 19. The compound according to claim 1, wherein R⁶ is selected from the group consisting of fluoro, chloro, bromo, methyl, methoxy, difluoromethyl, trifluoromethyl, difluoromethoxy and trifluoromethoxy.
 20. An agricultural composition containing at least one compound of claim 1 or an agriculturally acceptable salt thereof and at least one liquid or solid carrier.
 21. A method for controlling animal pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or a plant, plant propagation material, soil, area, material or environment in which the pests are growing or may grow, or the materials, plants, plant propagation material, soils, surfaces or spaces to be protected from pest attack or infestation with a pesticidally effective amount of a compound or a salt thereof as defined in claim
 1. 22. A method for protecting plant propagation material and/or the plants which grow therefrom, which method comprises treating the plant propagation material with a pesticidally effective amount of a compound or an agriculturally acceptable salt thereof as defined in claim
 1. 23. A plant propagation material, comprising at least one compound as defined in claim 1 or an agriculturally acceptable salt thereof.
 24. A method for treating or protecting an animal from infestation or infection by parasites which comprises bringing the animal in contact with a parasiticidally effective amount of a compound or a veterinarily acceptable salt thereof as defined in claim
 1. 